Vinyl Acetate → HCID 10518044, compound

HRID 2287502Notes

Reaction equation

HRID 2287502 reaction equation
[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][CH:6]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[CH:7]([OH:9])[CH3:8])[CH3:2].[C:22](OC=C)(=[O:24])[CH3:23]>C(N(CC)CC)C>[C:22]([O:9][C@@H:7]([C@H:6]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[CH2:5][CH:4]([O:19][CH2:20][CH3:21])[O:3][CH2:1][CH3:2])[CH3:8])(=[O:24])[CH3:23].[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[CH2:5][C@H:6]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[C@@H:7]([OH:9])[CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 7904Vinyl AcetateHCID 18705240(2RS,3RS)-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-ol

Product 2

HCID 10518044HCID 10518044, compoundHCID 57211167(2R,3S)-2-acetoxy-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentane

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
30 °C

Procedure

To 31.98 g of (2RS,3SR)-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-ol in 320 ml of vinyl acetate, 15.1 ml of triethylamine was added. The resulting reaction solution was stirred with 1.0 g of immobilized lipase (Toyozyme LIP) at 30° C. for 16 hours. After 0.9 g of immobilized lipase was further added, the solution was stirred at the same temperature for 46 hours. The insolubles were filtered off, and the filtrate was diluted with ethyl acetate, washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1→1/1] to give 18.40 g of (2R,3S)-2-acetoxy-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentane and 16.05 g of the title compound as colorless oily substances.

Workup

  1. customThe resulting reaction solution
  2. additionAfter 0.9 g of immobilized lipase was further added
  3. stirringthe solution was stirred at the same temperature for 46 hours
  4. filtrationThe insolubles were filtered off
  5. additionthe filtrate was diluted with ethyl acetate
  6. washwashed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered off
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1→1/1]

Sources & evidence

ORD record
ord-175577d64cf3468da06992095d71bf9d
Source dataset
uspto-grants-2000_07
Patent number
US06083985

Reaction notes

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