反応 #1755470

反応方程式

88

4-prop-2-ynyl-cyclohexanecarboxylic acid

CH2Cl2

MeOH

TMS Diazomethane

→

89

収率 80.0%

Methyl 4-prop-2-ynylcyclohexanecarboxylate

収率 80.0%

溶媒

acetic acid

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring
2. 2
   濃縮The reaction was concentrated in vacuo to an oil which
3. 3
   その他was purified by flash chromatography on silica gel

実験手順

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).

出典