Ethyl diazoacetate → Cyclobutoxyacetic Acid Ethyl Ester

HRID 18829ノート

反応式

HRID 18829 の反応式
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[N+](=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][O:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)[CH3:13]

参加物

6

反応物 2

HCID 12192Ethyl diazoacetateHCID 76218Cyclobutanol

生成物 1

HCID 62115785Cyclobutoxyacetic Acid Ethyl Ester収率 70.2%

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 cyclobutanol (720 mg, 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 140° C. to give 1.00 g of the product 469. 1H NMR (CDCl3) δ 4.21 (q, 2H), 4.03 (m, 1H), 3.98 (s, 2H), 2.28-2.15 (m, 2H), 2.08-1.95 (m, 2H), 1.7 (q, 1H), 1.50 (m, 1H), 1.28 (t, 3H)

後処理

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 140° C.

出典と根拠

ORDレコード
ord-bff3feea9180468ea0515afe85495ec3
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

反応ノート

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