Реакция #1755470

Уравнение реакции

88

4-prop-2-ynyl-cyclohexanecarboxylic acid

CH2Cl2

MeOH

TMS Diazomethane

→

89

Выход 80.0%

Methyl 4-prop-2-ynylcyclohexanecarboxylate

Выход 80.0%

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter stirring
2. 2
   КонцентрированиеThe reaction was concentrated in vacuo to an oil which
3. 3
   Другоеwas purified by flash chromatography on silica gel

Методика

To a solution of 88 (240 mg, 1.45 mmol) in 7:3 CH2Cl2:MeOH (10 mL) was added TMS Diazomethane (2.0 M in hexanes) (0.9 mL, 1.8 mmol) in 0.2 ml aliquots until the color remained yellow. The reaction was allowed to stir for an additional 0.25 hours at room temperature. After stirring, glacial acetic acid was added dropwise until the solution became colorless. The reaction was concentrated in vacuo to an oil which was purified by flash chromatography on silica gel using ether:petroleum ether (1:9) to yield 89 (210 mg, 80%) as a clear oil. 1H NMR (CDCl3) δ 3.60 (s, 3H), 2.25-2.13 (m, 1H), 2.08-1.94 (m, 3H), 1.95-1.90 (m, 2H), 1.49-1.31 (m, 3H), 1.10-0.93 (m, 2H); 13C NMR (CDCl3) δ 176.7, 83.3, 69.8, 51.9, 43.4, 36.7, 31.9, 29.2, 26.3; APCI m/z (rel intensity) 181 (MH+, 100).

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