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

HRID 18830

반응식

HRID 18830 반응식
[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]

참가 물질

6

반응물 2

HCID 12192Ethyl diazoacetateHCID 791041-Cyclopropylethanol

생성물 1

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

시약·촉매·용매 3

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 6344Dichloromethane용매HCID 8900Heptane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-57cf378cba194d43b0ed1030dd18ad65
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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