Cyclopentanol → Ethyl 2-(cyclopentyloxy)acetate

HRID 18821

반응식

HRID 18821 반응식
[CH:1]1([OH:6])[CH2:5][CH2:4][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:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:14]

참가 물질

6

반응물 2

HCID 7298CyclopentanolHCID 12192Ethyl diazoacetate

생성물 1

HCID 43119653Ethyl 2-(cyclopentyloxy)acetate수율 67.1%

시약·촉매·용매 3

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

실험 절차

To a solution of cyclopentanol (0.91 mL, 9.5 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 overnight. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue vacuum distilled at 150° C. to give 1.04 g of the product 444. 1H NMR (CDCl3) δ 4.21 (q, 2 H), 4.04 (s, 2 H), 1.85-1.45 (m, 8 H), 1.29 (t, 3 H)

후처리

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. distillationthe residue vacuum distilled at 150° C.

출처 및 근거

ORD 기록
ord-42c89541970c460c82e2aa4dc5db327e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

연결된 노트

불러오는 중…