ChemicalBook CAS DataBase List 1,6-HEPTADIEN-4-OL

1,6-HEPTADIEN-4-OL synthesis

11synthesis methods

Product Name:1,6-HEPTADIEN-4-OL
CAS Number:2883-45-6
Molecular formula:C7H12O
Molecular Weight:112.17

7319-38-2
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2883-45-6
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$41.00/1g

Yield:2883-45-6 82%

Reaction Conditions:

in tetrahydrofuran at -10 - 0; for 4 h;Inert atmosphere;

Steps:

Hepta-1,6-dien-4-ol (7)
To a solution of 6 (2.3 g, 32.81 mmol) in dry THF (10 mL), vinylmagnesium bromide (39.37 mL, 1.0 M solution in THF) was slowly added at-10°C and stirred 4 hours at 0°C. Saturated NH₄Cl solution (20 mL) was added to the mixture, which was slowly warmed to rt. The mixture was diluted with water (150 mL) and extracted with EtOAc (150 mL) two times. The combined organic layer was washed with brine, dried over anhydrous MgSO₄, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane, 1:10) to give 7 (3.02 g, 82%) as a colorless oil: ¹H NMR(CDCl₃, 300 MHz) δ 5.73-5.69 (m, 2H), 5.05-4.98(m, 4H), 3.31 (m, 1H), 2.13 (m, 4H); ¹³C NMR (CDCl₃, 75 MHz) δ 140.4,115.7, 74.7, 43.5.

References:

Shen, Guang Huan;Hong, Joon Hee [Nucleosides, nucleotides and nucleic acids,2014,vol. 33,# 1,p. 1 - 17]

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106-95-6 Synthesis