Vinyl Acetate → (-)-2-(4-Bromophenyl)-3-hydroxypropyl acetate

HRID 515458ノート

反応式

HRID 515458 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][OH:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.[C:13](OC=C)(=[O:15])[CH3:14]>>[C:13]([O:10][CH2:9][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH2:11][OH:12])(=[O:15])[CH3:14]

参加物

3

反応物 2

HCID 7904Vinyl AcetateHCID 218667012-(4-Bromophenyl)propane-1,3-diol

生成物 1

HCID 66718437(-)-2-(4-Bromophenyl)-3-hydroxypropyl acetate収率 65%

実験手順

To a solution of 2-(4-bromophenyl)propane-1,3-diol (9.01 g, 39.0 mmol) in vinyl acetate (100 ml) was added Lipase AK Amano (purchased from WAKO, 12.0 g) at room temperature. The mixture was stirred at room temperature for 11 hours and filtered through a pad of Celite to remove solid materials. After concentration, to the residue dissolved into ethanol (35 ml) and diisopropyl ether (200 ml) was added Lipase from porcine pancreas (type II, purchased from SIGMA, 22.2 g). The mixture was stirred at room temperature for 107 hours and filtered through a pad of Celite. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=2/1) to afford (−)-2-(4-bromophenyl)-3-hydroxypropyl acetate as colorless oil (6.88 g, 65%). [α]D=−11.2 (C=0.5, CHCl3).

後処理

  1. filtrationfiltered through a pad of Celite
  2. customto remove solid materials
  3. concentrationAfter concentration
  4. dissolutionto the residue dissolved into ethanol (35 ml) and diisopropyl ether (200 ml)
  5. additionwas added Lipase from porcine pancreas (type II, purchased from SIGMA, 22.2 g)
  6. stirringThe mixture was stirred at room temperature for 107 hours
  7. filtrationfiltered through a pad of Celite
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-44cece200af945b3b69b8d953d73c79e
出典データセット
uspto-grants-2015_08
特許番号
US09108957B2

反応ノート

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