Ethyl diazoacetate → Cyclooctyloxyacetic Acid Ethyl Ester

HRID 18813

반응식

HRID 18813 반응식
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>ClCCl.CCOCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:17]

참가 물질

6

반응물 2

HCID 12192Ethyl diazoacetateHCID 12766Cyclooctanol

생성물 1

HCID 68567541Cyclooctyloxyacetic Acid Ethyl Ester수율 37.8%

시약·촉매·용매 3

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of cyclooctanol (640 mg, 4.9 mmol) in dichloromethane (15 mL) is added rhodium (II) acetate dimer (21 mg) followed by ethyl diazoacetate (0.60 g, 5.7 mmol). The reaction mixture is stirred at RT for 10 min. The reaction mixture is rotary evaporated, and the residue dissolved in Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 397 mg of the product 413. 1H NMR (CDCl3) δ 4.21 (q, 2H), 4.06 (s, 2H), 3.50 (m, 1H), 1.93 (m, 2H), 1.7-1.4 (m, 8H), 1.4-1.3 (m, 2H), 1.28 (t, 3H); MS: m/z 215 (M++1).

후처리

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

출처 및 근거

ORD 기록
ord-37aa2452595246e29300b5370e97e95d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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