Methanol → Methyl 4-prop-2-ynylcyclohexanecarboxylate

HRID 1349975노트

반응식

HRID 1349975 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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).

후처리

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

출처 및 근거

ORD 기록
ord-5a704803b142422892b2069eb2cd3427
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214665B2

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