(4R)-4-[2-(Furan-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one → (4R)-4-[2-(Furan-2-yl)ethyl]-4-methyl-1,3-oxazolidin-2-one

HRID 422929Notes

Reaction equation

HRID 422929 reaction equation
[CH3:1][C@@:2]1([CH:8]=[CH:9][C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1>CO.[Pd]>[CH3:1][C@@:2]1([CH2:8][CH2:9][C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][O:5][C:4](=[O:7])[NH:3]1

Participants

4

Reactant 1

HCID 66672560(4R)-4-[2-(Furan-2-yl)ethenyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 66672687(4R)-4-[2-(Furan-2-yl)ethyl]-4-methyl-1,3-oxazolidin-2-oneYield 78.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of 10% palladium-charcoal (50% wet with water) (1.00 g) in methanol (20 ml) was added a solution of (4R)-4-methyl-4-[2-(furan-2-yl)ethenyl]-1,3-oxazolidin-2-one (10.04 g, 52.0 mmol) obtained in Reference example 3 in methanol (180 ml) with stirring, and the resulting mixture was stirred at room temperature under a hydrogen atmosphere for 40 minutes. After stirring, the palladium-charcoal in the reaction mixture was filtered off using celite, and the filtrate was evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (3:2-1:1) as the eluent to afford the title compound (7.95 g, yield: 78%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature under a hydrogen atmosphere for 40 minutes
  2. stirringAfter stirring
  3. filtrationthe palladium-charcoal in the reaction mixture was filtered off
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-4a627c22db69471cb974eb66a4b8870b
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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