Lipoamide → ethyl (3R)-3-hydroxy-3,6-dihydro-2H-pyran-4-carboxylate

HRID 1397198

반응식

HRID 1397198 반응식
[OH:1][CH:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH2:5][O:4][CH2:3]1.C(OC=C)(=O)CCCCC.C1C(CCCCC(N)=O)SSC1>C(OC(C)C)(C)C>[OH:1][C@@H:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH2:5][O:4][CH2:3]1

참가 물질

5

반응물 3

HCID 863LipoamideHCID 76451Vinyl hexanoateHCID 67329448ethyl 3-hydroxy-3,6-dihydro-2H-pyran-4-carboxylate

생성물 1

HCID 67328954ethyl (3R)-3-hydroxy-3,6-dihydro-2H-pyran-4-carboxylate수율 50.3%

시약·촉매·용매 1

HCID 7914Diisopropyl Ether용매

반응 조건

온도
35 °C

실험 절차

To a solution (380 mL) of ethyl 3-hydroxy-3,6-dihydro-2H-pyran-4-carboxylate (91.2 g) in diisopropyl ether were added vinyl hexanoate (150 mL) and Lipozyme IM (4.8 g). The reaction mixture was stirred at 35° C. for 24 hr and the insoluble material was filtered off. The obtained filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=6:1→1:1) to give the title compound (45.9 g, 50%).

후처리

  1. filtrationthe insoluble material was filtered off
  2. concentrationThe obtained filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0895eaf6cad8426ba6232aa5b156271a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901171B2

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