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

HRID 2053610

反応式

HRID 2053610 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, 1H), 7.19 (d, 1H), 6.95-6.90 (m, 2H), 4.30 (s, 2H), 4.25-4.15 (m, 4H), 4.0 (t, 2H), 1.2 (t, 3H); 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-abacd520fa7a45a4a3d6e9e6442ca255
出典データセット
uspto-grants-2008_02
特許番号
US07326792B2

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