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

HRID 18833

반응식

HRID 18833 반응식
[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]

참가 물질

6

반응물 2

HCID 7360Tetrahydrofurfuryl alcoholHCID 12192Ethyl diazoacetate

생성물 1

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

시약·촉매·용매 3

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 6344Dichloromethane용매HCID 8900Heptane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-204f5de948154c3eb146710bb643fd31
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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