Iodine → Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionate

HRID 1685813노트

반응식

HRID 1685813 반응식
Br[CH:2]1[CH2:6][CH2:5][S:4][C:3]1=[O:7].[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=1)=[O:9].II>O1CCCC1.[Zn]>[OH:9][CH:8]([CH:2]1[CH2:6][CH2:5][S:4][C:3]1=[O:7])[C:10]1[CH:11]=[CH:12][C:13]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=1

참가 물질

6

반응물 3

HCID 807IodineHCID 127428403-Bromothiolan-2-oneHCID 13066570rac 2-(4-Formylphenyl)propionic Acid Ethyl Ester

생성물 1

HCID 59202209Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionate수율 23.6%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

실험 절차

3-Bromothiolan-2-one (315 mg) and ethyl 2-(4-formylphenyl)propionate (300 mg) were dissolved in tetrahydrofuran, and to the solution was added zinc (147 mg) and a catalytic amount of iodine, and the reaction mixture was heated until the mixture was refluxed. The reaction mixture was stirred overnight at room temperature, then the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (106 mg, 20%).

후처리

  1. temperaturewas refluxed
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-bef886875c0241d4bfe00165b1b226a0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148421B2

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