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

HRID 1803634노트

반응식

HRID 1803634 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 7909Methyl Isobutyl Ketone용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-7a7055bfdc3643848fa0333f0a44ce1f
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08350090B1

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