Ethyl diazoacetate → Ethyl [(3-methoxyphenyl)methoxy]acetate

HRID 18806

反応式

HRID 18806 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:18]

参加物

6

反応物 2

HCID 12192Ethyl diazoacetateHCID 814373-Methoxybenzyl alcohol

生成物 1

HCID 28940145Ethyl [(3-methoxyphenyl)methoxy]acetate収率 99.1%

試薬・触媒・溶媒 3

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒HCID 8900Heptane溶媒

実験手順

To a solution of 3-methoxybenzyl alcohol (1.24 g, 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 150° C. to give 2.00 g of the product 398. 1H NMR (CDCl3) δ 7.26 (t, 1H), 6.93 (m, 2H), 6.85 (m, 1H), 4.62 (s, 2H), 4.23 (q, 2H), 4.09 (s, 2H), 3.81 (s, 3H), 1.29 (t, 3H); MS: m/z 224 (M++1).

後処理

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

出典と根拠

ORDレコード
ord-341b35e602af476d9d8ada35dc20b078
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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