Vinyl Acetate → (R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate

HRID 1803634ノート

反応式

HRID 1803634 の反応式
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:3]1.[C:17](OC=C)(=[O:19])[CH3:18]>CC(CC(C)C)=O>[C:17]([O:1][C@@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[CH:3]1)(=[O:19])[CH3:18]

参加物

4

反応物 2

HCID 7904Vinyl AcetateHCID 711700384-Hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone

生成物 1

HCID 71170032(R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate

試薬・触媒・溶媒 1

HCID 7909Methyl Isobutyl Ketone溶媒

実験手順

4-Hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone (9 g, 41.26 mmol) was dissolved in isobutyl methyl ketone (90 mL), and vinyl acetate (8.4 g, 97.57 mmol) and Lipase derived from Alcaligenese spp. (0.9 g) were added to the solution, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered to remove Lipase and the filtrate was evaporated. The resulting residue was purified by chromatography on a silica gel column using hexane-EtOAc as eluent to give (R)-3-(3-methoxybenzyl)-4-oxocyclopent-2-enyl acetate as yellow oil: 4.29 g (95% ee by HPLC using a chiral column) and (S)-4-hydroxy-2-(3-methoxybenzyl)cyclopent-2-enone as yellow oil: 4.05 g (100% ee by HPLC using a chiral column)

後処理

  1. addition(0.9 g) were added to the solution
  2. filtrationThe reaction mixture was filtered
  3. customto remove Lipase
  4. customthe filtrate was evaporated
  5. customThe resulting residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-7a7055bfdc3643848fa0333f0a44ce1f
出典データセット
uspto-grants-2013_01
特許番号
US08350090B1

反応ノート

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