Ethyl diazoacetate → Cyclooctyloxyacetic Acid Ethyl Ester

HRID 18813

反応式

HRID 18813 の反応式
[CH:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N-]>ClCCl.CCOCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][O:9][CH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:17]

参加物

6

反応物 2

HCID 12192Ethyl diazoacetateHCID 12766Cyclooctanol

生成物 1

HCID 68567541Cyclooctyloxyacetic Acid Ethyl Ester収率 37.8%

試薬・触媒・溶媒 3

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of cyclooctanol (640 mg, 4.9 mmol) in dichloromethane (15 mL) is added rhodium (II) acetate dimer (21 mg) followed by ethyl diazoacetate (0.60 g, 5.7 mmol). The reaction mixture is stirred at RT for 10 min. The reaction mixture is rotary evaporated, and the residue dissolved in Et2O, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 397 mg of the product 413. 1H NMR (CDCl3) δ 4.21 (q, 2H), 4.06 (s, 2H), 3.50 (m, 1H), 1.93 (m, 2H), 1.7-1.4 (m, 8H), 1.4-1.3 (m, 2H), 1.28 (t, 3H); MS: m/z 215 (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-37aa2452595246e29300b5370e97e95d
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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