Methanol → Methyl 4-prop-2-ynylcyclohexanecarboxylate

HRID 1349975ノート

反応式

HRID 1349975 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 10749876Methyl 4-prop-2-ynylcyclohexanecarboxylate収率 80%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5a704803b142422892b2069eb2cd3427
出典データセット
uspto-grants-2007_05
特許番号
US07214665B2

反応ノート

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