Reaktion #1755470

Reaktionsgleichung

88

4-prop-2-ynyl-cyclohexanecarboxylic acid

CH2Cl2

MeOH

TMS Diazomethane

→

89

Ausbeute 80.0%

Methyl 4-prop-2-ynylcyclohexanecarboxylate

Ausbeute 80.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle