Réaction #44335

Équation de réaction

88

4-prop-2-ynyl-cyclohexanecarboxylic acid

CH2Cl2

MeOH

TMS Diazomethane

→

89

Rendement 80.0%

Methyl 4-prop-2-ynylcyclohexanecarboxylate

Rendement 80.0%

Solvants

acetic acid

Conditions de réaction

Traitement

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

Mode opératoire

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, 1 H), 2.08-1.94 (m, 3 H), 1.95-1.90 (m, 2 H), 1.49-1.31 (m, 3 H), 1.10-0.93 (m, 2 H); 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).

Source