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CAS No. : | 13781-67-4 | MDL No. : | MFCD00009766 |
Formula : | C6H8OS | Boiling Point : | - |
Linear Structure Formula : | SC4H3CH2CH2OH | InChI Key : | YYPNNBPPDFTQFX-UHFFFAOYSA-N |
M.W : | 128.19 | Pubchem ID : | 83731 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Step 2: 2-(thiophen-3-yl)ethanol Tetrahydrofuran (200 mL) was added to LiAlH4 (4.56 g, 0.12 mol) and the mixture was stirred at 0 C. 2-(thiophen-3-yl)acetic acid (14.2 g, 0.1 mol) in THF (100 mL) was added dropwise at this temperature. After the addition, the reaction mixture was stirred at 0 C. for further 2 hours. To the reaction mixture was added EtOAc (200 mL) slowly and then 5 mL of water. The suspension was filtered though ceilite, the filtrate was dried over anhydrous sodium sulfate and concentrated to dryness to afford 2-(thiophen-3-yl)ethanol (12.44 g, yield: 99%). 1H NMR (MeOD, 400 MHz): δ5.92-5.87 (m, 1H), 5.69-5.66 (m, 1H), 5.57 (s, 1H) 2.90 (d, J=14.0 Hz, 1H), 2.38 (d, J=14 Hz, 1H), 1.55-1.42 (m, 2H). | |
98% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 3h;Schlenk technique; Inert atmosphere; | In a flame-dried Schlenk flask, equipped with a magnetic stirring bar, an argon inlet, and a septum, LiAlH4 (5.7 g, 150 mmol, 1.5 equiv) was dissolved in THF (100 mL) at 0 C. A solution of 3-thienylacetic acid (3, 14.2 g, 100 mmol, 1.0 equiv) in THF (50 mL) at 0 C was added dropwise. The mixture was stirred for 3 h at 0 C and then it was carefully quenched with EtOAc and EtOH. Subsequently, 1-2% NaOH (20 mL) was added and the mixture was stirred for 1 h, allowing aluminum hydroxide to precipitate as a granular solid. Finally, the mixture was filtered over Celite. The collected organic layers were dried (MgSO4), and the solvent was evaporated in vacuo to give the pure alcohol 4 (12.5 g, 98%) as a pale yellow oil. |
78% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 7h; | To a 0 C cooled stirred suspension of lithium aluminiumhydride (8.0 g, 0.21 mol) in THF (100 mL) was added 3-Thiopheneaceticacid 01 (20 g, 0.14 mol) in THF (100 mL) drop wise over1 h. Reaction mixture was warmed to room temperature and stirredfor 6 h. Reaction progress was checked by TLC for completionand then quenched with 10% NaOH solution. The mixture was filteredover Celite, washed with ethylacetate. Aqueous layer wasextracted with ethylacetate and the combined organic layer waswashed with brine. Dried over sodium sulfate and concentratedto yield 2 as a yellow liquid (14.2 g, 78%) 1H NMR (MeOD, 400MHz): d 5.92-5.87 (m, 1H), 5.69-5.66 (m, 1H), 5.57 (s, 1H) 2.90(d, J = 14.0 Hz, 1H), 2.38 (d, J = 14 Hz, 1H), 1.55-1.42 (m, 2H). 13CNMR (DMSO d6, 100 MHz): 145.53, 129.13, 126.54, 121.45,64.46, 38.85; ESI-MS m/z: (Calcd for C6H8OS: 128.03); Found:128.9 [M+H]+. |
With lithium aluminium tetrahydride;Inert atmosphere; | General procedure: The majority of alcohols were commercially available. Alcohols 9c,26 9i,27 9j28 and 9k29 were prepared by LiAlH4 reduction of the corresponding carboxylic acids and gave spectral data consistent with those in the literature. | |
3.59 g | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 1.25h; | Step 1: 2-(3-Thienyl)ethanol [00367] A solution of thiophene-3-acetic acid (4.982 g, 35.04 mmol) in THF ( 120 mL, 1500 mmol) was cooled to 0 C, and lithium tetrahydroaluminate ( 1 .596 g, 42.05 mmol) was added slowly over 15 min. The reaction was allowed to warm to rt and stirred for 2hrs. The reaction was quenched via addition of water (5 mL) and EtOAc ( 10ml). The mixture was filtered, and the filter cake was washed with 30ml EtOAc. The filtrate was concentrated in vacuo to afford the title compound (3.59 g). NMR (400 MHz, Chloroform-d) δ 7.31 (dd, J = 4.9, 3.0 Hz, 1 H), 7.1 1 - 7.05 (m, 1 H), 7.05 - 6.97 (m, 1 H), 3.87 (t, J = 6.4 Hz, 2H), 2.92 (t, J = 6.4 Hz, 2H), 1.71 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; | Example 7; 2-Iodo-3-(2-thiophen-3-yl-ethoxy)-pyridine; 13 To a solution containing <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> 12 (1.85 g, 8.37 mmol), 2-(3-thienyl)ethanol (1.20 mL, 10.9 mmol), and triphenylphosphine (2.85 g, 10.9 mmol) in tetrahydrofuran (46.2 mL, 5.70 mmol) was added diisopropyl azodicarboxylate (2.14 mL, 10.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and purified by flash chromatography EtOAc/Hex (0-100%) eluted at 30% to give 13 (yield 90%). MS: (ESI+) 332.2 |
90% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 18h; | Step 1: 2-Iodo-3-(2-thiophen-3-yl-ethoxy)-pyridine To a solution containing <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (1.85 g, 8.37 mmol), 2-(3-thienyl)ethanol (1.20 mL, 10.9 mmol), and triphenylphosphine (2.85 g, 10.9 mmol) in tetrahydrofuran (46.2 mL, 5.70 mmol) was added diisopropyl azodicarboxylate (2.14 mL, 10.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and purified by flash chromatography EtOAc/Hex (0-100%) eluted at 30% to give 2-Iodo-3-(2-thiophen-3-yl-ethoxy)-pyridine (yield 90%). MS: (ESI+) 332.2 |
[ 70260-16-1 ]
(2-Bromothiophen-3-yl)methanol
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