Ethyl diazoacetate → (1-Cyclopropyl-1-ethoxy)acetic Acid Ethyl Ester

HRID 18830

反応式

HRID 18830 の反応式
[CH:1]1([CH:4]([OH:6])[CH3:5])[CH2:3][CH2:2]1.[N+](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][O:6][CH:4]([CH:1]1[CH2:3][CH2:2]1)[CH3:5])[CH3:14]

参加物

6

反応物 2

HCID 12192Ethyl diazoacetateHCID 791041-Cyclopropylethanol

生成物 1

HCID 68565879(1-Cyclopropyl-1-ethoxy)acetic Acid Ethyl Ester収率 71.6%

試薬・触媒・溶媒 3

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒HCID 8900Heptane溶媒

実験手順

To a solution of cyclopropyl-1-ethanol (860 mg, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at rt for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 130° C. to give 1.11 g of the product 471. 1H NMR (CDCl3) δ 4.12 (s, 2H), 4.10 (q, 2H), 2.86 (m, 1H), 1.25-1.15 (m, 6H), 0.8-0.7 (m, 1H), 0.55-0.3 (m, 3H), 0.05-0.02 (m, 1H); MS: m/z 173 (M++1).

後処理

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 130° C.

出典と根拠

ORDレコード
ord-57cf378cba194d43b0ed1030dd18ad65
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

読み込み中…