Methanol → 2-[2-(2-Chlorophenoxy)ethoxy]acetic Acid Ethyl Ester

HRID 18819

반응식

HRID 18819 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[N+](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-].CO>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:7][CH2:6][CH2:5][O:4][C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[Cl:1])[CH3:19]

참가 물질

6

반응물 3

HCID 887MethanolHCID 12192Ethyl diazoacetateHCID 849332-(2-Chlorophenoxy)ethanol

생성물 1

HCID 685707682-[2-(2-Chlorophenoxy)ethoxy]acetic Acid Ethyl Ester수율 52.6%

시약·촉매·용매 2

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

실험 절차

To a solution of 2-(2-chlorophenoxy)ethanol (1.73 mL, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (11 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at rt for 20 min. To the reaction mixture is added MeOH followed by rotary evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (25:75) gives 1.36 g of the product 436. 1H NMR (CDCl3) δ 7.35 (d, 1 H), 7.19 (d, 1 H), 6.95-6.90 (m, 2 H), 4.30 (s, 2 H), 4.25-4.15 (m, 4 H), 4.0 (t, 2 H), 1.2 (t, 3 H); MS: m/z 259 (M++1).

후처리

  1. customthe residue is purified by chromatography on silica gel
  2. washelution with EtOAc:heptane (25:75)

출처 및 근거

ORD 기록
ord-45a00ca672ec405ca7852abcbc0f4552
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

연결된 노트

불러오는 중…