Ethyl diazoacetate → Cyclobutoxyacetic Acid Ethyl Ester

HRID 18829노트

반응식

HRID 18829 반응식
[CH:1]1([OH:5])[CH2:4][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][CH:1]1[CH2:4][CH2:3][CH2:2]1)[CH3:13]

참가 물질

6

반응물 2

HCID 12192Ethyl diazoacetateHCID 76218Cyclobutanol

생성물 1

HCID 62115785Cyclobutoxyacetic Acid Ethyl Ester수율 70.2%

시약·촉매·용매 3

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

실험 절차

To a solution of cyclobutanol (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 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 140° C. to give 1.00 g of the product 469. 1H NMR (CDCl3) δ 4.21 (q, 2H), 4.03 (m, 1H), 3.98 (s, 2H), 2.28-2.15 (m, 2H), 2.08-1.95 (m, 2H), 1.7 (q, 1H), 1.50 (m, 1H), 1.28 (t, 3H)

후처리

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 140° C.

출처 및 근거

ORD 기록
ord-bff3feea9180468ea0515afe85495ec3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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