(3S,5R)-3-((E)-but-2-enyl)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one → (3S,5R)-3-butyl-5-(4-fluorophenyl)dihydrofuran-2(3H)-one

HRID 1643270Notes

Reaction equation

HRID 1643270 reaction equation
[CH2:1]([C@H:5]1[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[O:7][C:6]1=[O:17])/[CH:2]=[CH:3]/[CH3:4]>C1C=CC=CC=1>[CH2:1]([C@H:5]1[CH2:9][C@H:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[O:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 1

HCID 59568805(3S,5R)-3-((E)-but-2-enyl)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one

Product 1

HCID 59568766(3S,5R)-3-butyl-5-(4-fluorophenyl)dihydrofuran-2(3H)-oneYield 92.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(3S,5R)-3-((E)-but-2-enyl)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one (100.0 mg, 0.43 mmol) was dissolved into 8 mL benzene and to it added Wilkinson catalysis (39.0 mg, 0.4 mmol). The solution was saturated with H2 (stream of H2 bubbled through solution) and then stirred for 20 h at room temperature under an atmosphere of hydrogen balloon. The solvent was removed under reduced pressure and the product isolated by flash column chromatography eluting with 3% to 30% ethyl acetate/hexane to give 94 mg of the title compound as a colorless oil.

Workup

  1. additionadded Wilkinson catalysis (39.0 mg, 0.4 mmol)
  2. customThe solvent was removed under reduced pressure
  3. customthe product isolated by flash column chromatography
  4. washeluting with 3% to 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6e9fd58f1c5447268da45deb03134004
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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