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

HRID 1685813ノート

反応式

HRID 1685813 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-bef886875c0241d4bfe00165b1b226a0
出典データセット
uspto-grants-2012_04
特許番号
US08148421B2

反応ノート

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