Tetrahydrofurfuryl alcohol → (Tetrahydrofuran-2-ylmethoxy)acetic Ethyl Ester

HRID 18833

反応式

HRID 18833 の反応式
[CH2:1]([OH:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[N+](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:7][CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][O:6]1)[CH3:15]

参加物

6

反応物 2

HCID 7360Tetrahydrofurfuryl alcoholHCID 12192Ethyl diazoacetate

生成物 1

HCID 43119675(Tetrahydrofuran-2-ylmethoxy)acetic Ethyl Ester収率 60.2%

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 tetrahydrofurfuryl alcohol (1.02 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 130° C. to give 1.02 g of the product 477. 1H NMR (CDCl3) δ 4.11 (q, 2H), 4.10 (s, 2H), 3.93 (m, 1H), 3.72 (m, 1H), 3.61 (m, 1H), 3.44 (m, 2H), 1.95-1.75 (m, 3H), 1.61-1.53 (m, 1H), 1.20 (t, 3H).

後処理

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 130° C.

出典と根拠

ORDレコード
ord-204f5de948154c3eb146710bb643fd31
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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