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2-[4-[(E)-2-methoxyethenyl]phenyl]-pyrazine[ No CAS ]
[ 127406-08-0 ]
Yield
Reaction Conditions
Operation in experiment
820 mg (71%)
With sodium hexamethyldisilazane; In tetrahydrofuran;
Step A 2-[4-[(E)-2-methoxyethenyl]phenyl]-pyrazine Sodium hexamethyldisilazide (10.80 mL, 10.80 mmol, 11.0M in THF) was added to a suspension of methoxymethyltriphenylphosphonium chloride (3.72 g, 10.80 mmol) in THF (20 mL) at -10 C., and the red-orange mixture was stirred for 15 min at -10 C. A solution of 4-pyrazinylbenzaldehyde (1.00 g, 5.43 mmol) prepared as described in reference example 17) in THF (3 mL) was added dropwise, and stirring was continued at -10 C. for 1 h. The reaction mixture was quenched with sat. aq. NH4Cl, extracted with ethyl acetate, the organic layer dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 3:1 hexane/ethyl acetate) yielded 820 mg (71%) of the title compound (E:Z=1:1). MS 213 (M+H)+.
8-(4-(methoxymethylene)cyclohexyl)-1,4-dioxaspiro[4.5]decane[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
To a stirring solution of (methoxymethyl)triphenylphosphonium chloride (3.74 g, 10.91 mmol) in THF (16 mL) was added potassium tert-butoxide (1.224 g, 10.91 mmol) portionwise. The solution was stirred at room temperature for 50 min then a solution of <strong>[56309-94-5]4-(1,4-dioxaspiro[4.5]decan-8-yl)cyclohexanone</strong> (2 g, 8.39 mmol) in THF (16 mL) was added slowly. The reaction mixture was stirred for 3.5 h. The solvent was removed under vacuum. The residue was treated with Et2O (44 mL) and stirred for 1 h. The mixture was filtered, washed with Et2O (2 x 50 mL) and the filtrate was evaporated. The crude product was purified by column chromatography (EA/Iso- hexane) to afford 1.8 g (76percent) of 8-(4-(methoxymethylene)cyclohexyl)-l ,4- dioxaspiro[4.5]decane as a colourless oil.
tert-butyl 6-(methoxymethylene)-2-azaspiro[3.3]heptane-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
To a solution of (methoxymethyl)triphenylphosphonium chloride (2.92 g, 8.52 mmol) in THF (20 mL) was added dropwise LDA (4.47 ml, 8.95 mmol, 1.0 M in THF) over 20 mm under N2 at 0 °C. The reaction mixture was stirred at room temperature for 2 h. Then a solution of tertbutyl 6-oxo-2-azaspiro[3.3jheptane-2-carboxylate (900 mg, 4.26 mmol) in THF (10 mL) was added dropwise to the mixture. The reaction mixture was stirred at 60 °C for 3 h, thenquenched with water (30 mL) and extracted with ethyl acetate (20 mL x 3). The combined organic layers were washed with water (40 mL) and brine (40 mL), dried over anhydrous MgSO4 and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluted with PE / EtOAc (50:1- 20: 1, v/v) to give the title compound. ?H NMR (400 MI-Tz, CDC13): oe = 5.81 (s, 1H), 3.93(s, 4H), 3.56 (s, 3H), 2.87 (s, 2H), 2.79 (s, 2H), 1.44 (s, 12H).
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