Water → HCID 19776899, compound

HRID 1612874Notes

Reaction equation

HRID 1612874 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[S:13][C:12]3[C:14]([O:19][CH3:20])=[CH:15][C:16]([CH3:18])=[CH:17][C:11]=3[CH2:10][O:9][C:8](=[O:21])[C:7]=2[C:22]=1[O:23][CH3:24].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:26].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C)C=O>[C:2]([C:3]1[CH:4]=[CH:5][C:6]2[S:13][C:12]3[C:14]([O:19][CH3:20])=[CH:15][C:16]([CH3:18])=[CH:17][C:11]=3[CH2:10][O:9][C:8](=[O:21])[C:7]=2[C:22]=1[O:23][CH3:24])([OH:26])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 19776900HCID 19776900, compound

Product 1

HCID 19776899HCID 19776899, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

560 mg (1.62 mmol) of the compound from Example VI are stirred overnight at 25° C. with 9.13 g (24.3 mmol) of pyridinium dichromate in 20 ml of dimethylformamide. The mixture is poured into water and washed with ether, the ether phase is washed with water and dried over sodium sulphate and, after concentrating in vacuo, the residue is chromatographed on silica gel using methylene chloride/ethanol 10:1.

Workup

  1. washwashed with ether
  2. washthe ether phase is washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationafter concentrating in vacuo
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-a7e05b59994e45a293b849006814a6df
Source dataset
uspto-grants-1993_03
Patent number
US05190971

Reaction notes

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