Cornforth reagent → HCID 54193301, compound

HRID 1981221Notes

Reaction equation

HRID 1981221 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5]([CH:8]([CH:17]1[O:22][C:21](=[O:23])[CH2:20][CH2:19][CH2:18]1)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:7])=[O:6].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:25].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O.O>[C:2]([CH2:3][CH2:4][S:5]([CH:8]([CH:17]1[O:22][C:21](=[O:23])[CH2:20][CH2:19][CH2:18]1)[CH:9]=[CH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:6])=[O:7])([OH:25])=[O:1]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 54037153HCID 54037153, compound

Product 1

HCID 54193301HCID 54193301, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-[1-(hydroxypropylsulphonyl)-3-phenyl-2-propenyl]tetrahydro-2H-pyran-2-one, (see Example 24) (1.0 g) and pyridinium dichromate (4.67 g) in dimethyl formamide (10 ml) was stirred at room temperature for 20 hours. The mixture was diluted with water and extracted with ethyl acetate to give 6-[1-(carboxyethylsulphonyl)-3-phenyl-2-propenyl]tetrahydro-2H-pyran-2-one as an oil. The lactone was hydrolysed and the disodium salt prepared, as described in Example 22(b) to give the disodium salt of the title compound, m.p. about 203° C.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-a3a5f9cbf55f48f1bddc41dc4f0d3d3e
Source dataset
uspto-grants-1985_04
Patent number
US04513005

Reaction notes

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