Methanol → Methyl 4-prop-2-ynylcyclohexanecarboxylate

HRID 1349975Notes

Reaction equation

HRID 1349975 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3].[CH2:13](Cl)Cl.CO.[Si](C=[N+]=[N-])(C)(C)C>C(O)(=O)C>[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 107971444-Prop-2-ynylcyclohexanecarboxylic acid

Product 1

HCID 10749876Methyl 4-prop-2-ynylcyclohexanecarboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  1. stirringAfter stirring
  2. concentrationThe reaction was concentrated in vacuo to an oil which
  3. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5a704803b142422892b2069eb2cd3427
Source dataset
uspto-grants-2007_05
Patent number
US07214665B2

Reaction notes

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