HCID 69365855, compound → 4-(2-Phenylethyl)oxolan-2-one

HRID 8196Notes

Reaction equation

HRID 8196 reaction equation
CO[C:3](=[O:23])[CH:4]=[C:5]([CH2:14][O:15]CC1C=CC=CC=1)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Pd].C(O)(=O)C>[CH2:6]([CH:5]1[CH2:14][O:15][C:3](=[O:23])[CH2:4]1)[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 69365855HCID 69365855, compound

Product 1

HCID 137049024-(2-Phenylethyl)oxolan-2-oneYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 3-benzyloxymethyl-5-phenyl-pent-2-enoic acid methyl ester, (3.2 g, 13.5 mmol), 10 wt. % palladium on activated carbon (3.2 g), and acetic acid (40 mL) is placed in a Parr® Shaker under hydrogen (45 PSI) and shaken 4 h. The mixture is filtered through a pad of Celite® and concentrated in vacuo. The residue is dissolved in toluene (30 mL), treated with p-tolunesulfonic acid (0.1 g), refluxed for 2 h and concentrated in vacuo. The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes then 50% ethyl acetate/hexanes) to yield the title compound 1.2 g (62%) as a colorless liquid.

Workup

  1. filtrationThe mixture is filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in toluene (30 mL)
  4. additiontreated with p-tolunesulfonic acid (0.1 g)
  5. temperaturerefluxed for 2 h
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d114d255e7104c6da67a11cdcb488991
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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