Water → 2-Oxobicyclo[4.1.0]heptane-1-acetic Acid Ethyl Ester

HRID 2351372ノート

反応式

HRID 2351372 の反応式
[I-].[CH3:2][S+](C)(C)=O.[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH:13]=1)[CH3:8].O>CS(C)=O>[CH2:7]([O:9][C:10](=[O:19])[CH2:11][C:12]12[CH2:2][CH:13]1[CH2:14][CH2:15][CH2:16][C:17]2=[O:18])[CH3:8]

参加物

5

反応物 3

HCID 962WaterHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 115792286-Oxo-1-cyclohexeneacetic acid ethyl ester

生成物 1

HCID 147702072-Oxobicyclo[4.1.0]heptane-1-acetic Acid Ethyl Ester収率 76.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

Sodium hydride (18.1 mmol, 543 mg of an 80% dispersion in mineral oil) was washed with 2×5 mL of petroleum ether under nitrogen, then it was dried and trimethylsulfoxonium iodide (3.99 g, 18.1 mmol) was added to the flask followed by 21.6 mL dimethylsulfoxide added dropwise. Next, a solution of 6-oxo-1-cyclohexeneacetic acid ethyl ester (2.90 g, 17.3 mmol) was added dropwise as a solution in 4.5 mL of dimethylsulfoxide as the reaction mixture was cooled with a water bath. After the addition, the reaction mixture was stirred at room temperature for 1.5 hours then poured into 80 mL of cold water and extracted with 4×60 mL of ether. The extracts were combined, washed with 80 mL of brine, dried over magnesium sulfate and concentrated affording 2.4 g (13.2 mmol, 73% yield) of the title compound as a yellow oil.

後処理

  1. washSodium hydride (18.1 mmol, 543 mg of an 80% dispersion in mineral oil) was washed with 2×5 mL of petroleum ether under nitrogen
  2. customit was dried
  3. additionadded dropwise
  4. temperaturewas cooled with a water bath
  5. additionAfter the addition
  6. extractionextracted with 4×60 mL of ether
  7. washwashed with 80 mL of brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-339b3983f752429cbe90cfcc59c85b4c
出典データセット
uspto-grants-1989_10
特許番号
US04873257

反応ノート

読み込み中…