5-[3-(Benzyloxy)propyl]-3-hydroxy-4-phenylfuran-2(5H)-one → 3-Hydroxy-5-(3-hydroxypropyl)-4-phenylfuran-2(5H)-one

HRID 1381370Notes

Reaction equation

HRID 1381370 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH:12]1[O:16][C:15](=[O:17])[C:14]([OH:18])=[C:13]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C1C=CC=CC=1>CO.[Pd]>[OH:18][C:14]1[C:15](=[O:17])[O:16][CH:12]([CH2:11][CH2:10][CH2:9][OH:8])[C:13]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 133895795-[3-(Benzyloxy)propyl]-3-hydroxy-4-phenylfuran-2(5H)-one

Product 1

HCID 133895803-Hydroxy-5-(3-hydroxypropyl)-4-phenylfuran-2(5H)-oneYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-(3-Benzyloxypropyl)-3-hydroxy-4-phenyl-2(5H)-furanone (65 mg) was dissolved in methanol (20 ml), and palladium black (20 mg) was added. Catalytic reduction was carried out in ordinary temperature and atmosphere. After completion of the reaction, the palladium black was filtered off and the methanol was distilled off under reduced pressure. The crude crystals thus obtained were recrystallized from chloroform to give 3-hydroxy-5-(3-hydroxypropyl)-4-phenyl-2(5H)-furanone (45 mg). m.p. 148°-150° C.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe palladium black was filtered off
  3. distillationthe methanol was distilled off under reduced pressure
  4. customThe crude crystals thus obtained
  5. customwere recrystallized from chloroform

Sources & evidence

ORD record
ord-79b8cd25168d4310a9c74c2cf5db80ae
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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