반응 #1755470

반응 방정식

88

4-prop-2-ynyl-cyclohexanecarboxylic acid

CH2Cl2

MeOH

TMS Diazomethane

→

89

수율 80.0%

Methyl 4-prop-2-ynylcyclohexanecarboxylate

수율 80.0%

용매

acetic acid

반응 조건

후처리

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

실험 절차

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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