Ethyl diazoacetate → (3-Trifluoromethylbenzyloxy)acetic Acid Ethyl Ester

HRID 18804

反応式

HRID 18804 の反応式
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[N+](=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([C:2]([F:11])([F:12])[F:1])[CH:4]=1)[CH3:20]

参加物

6

反応物 2

HCID 12192Ethyl diazoacetateHCID 676813-(Trifluoromethyl)benzylic alcohol

生成物 1

HCID 68572230(3-Trifluoromethylbenzyloxy)acetic Acid Ethyl Ester収率 97.9%

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-trifluoromethylbenzyl alcohol (1.62 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 2.31 g of the product 394. 1H NMR (CDCl3) δ 7.65 (bs, 1H), 7.57 (m, 2H), 7.48 (t, 1H), 4.69 (s, 2H), 4.24 (q, 2H), 4.14 (s, 2H), 1.30 (t, 3H); MS: m/z 263 (M+).

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-4849db3f64cf446ca8fa05063e74d175
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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