Ethyl diazoacetate → Ethyl 2-(cyclopropylmethoxy)acetate

HRID 18827

반응식

HRID 18827 반응식
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[N+](=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)[CH3:13]

참가 물질

6

반응물 2

HCID 12192Ethyl diazoacetateHCID 75644Cyclopropanemethanol

생성물 1

HCID 43119684Ethyl 2-(cyclopropylmethoxy)acetate수율 85.7%

시약·촉매·용매 3

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

실험 절차

To a solution of cyclopropylmethanol (720 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 5 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.22 g of the product 462. 1H NMR (CDCl3) δ 4.2 (q, 2H), 4.09 (s, 2H), 3.37 (d, 2H), 1.27 (t, 3H), 1.09 (m, 1H), 0.56-0.51 (m, 2H), 0.25-0.2 (m, 211); MS: m/z 191 (M+)

후처리

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 150° C.

출처 및 근거

ORD 기록
ord-43fbd85eb1b048678a5364b29514bed8
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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