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

HRID 18819

反応式

HRID 18819 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-45a00ca672ec405ca7852abcbc0f4552
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

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