HCID 19096630, compound → HCID 12711612, compound

HRID 486853Notes

Reaction equation

HRID 486853 reaction equation
[Cl:1][CH2:2][C:3]1[O:8][C:7](=[O:9])[CH2:6][CH2:5][CH:4]=1>[C].[Pd].C(OCC)(=O)C>[Cl:1][CH2:2][CH:3]1[O:8][C:7](=[O:9])[CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 1

HCID 19096630HCID 19096630, compound

Product 1

HCID 12711612HCID 12711612, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 150 mg (1.024 mmol) of (-)-6-chloromethyldihydropyran-2-one obtained in Example 4, 6 ml of ethyl acetate and 60 mg of 10% palladium-carbon was stirred for 2 hours under hydrogen atmosphere. After completion of the reaction, the catalyst was removed by filtration, and the solvent was distilled off. Afterward, the resultant residue was subjected to column chromatography (an eluent of hexane:ethyl acetate=5:1), thereby obtaining 146 mg (yield 96%) of (-)-6-chloromethyltetrahydropyran-2-one having

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed by filtration
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-e7c9c0401dd84bdc93bb8e680c2a9deb
Source dataset
uspto-grants-1994_03
Patent number
US05292891

Reaction notes

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