Methanol → HCID 15058197, compound

HRID 704658Notes

Reaction equation

HRID 704658 reaction equation
CO.[C:3]1([CH:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:10][C:11]2[C:16](=[O:17])[CH:15]=[C:14]([CH2:18][OH:19])[N:13]([CH:20]([CH3:22])[CH3:21])[CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>[O-2].[O-2].[Mn+4].C1C=CC=CC=1.C(OCC)(=O)C>[C:23]1([CH:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[O:10][C:11]2[C:16](=[O:17])[CH:15]=[C:14]([CH:18]=[O:19])[N:13]([CH:20]([CH3:22])[CH3:21])[CH:12]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 15058196HCID 15058196, compound

Product 1

HCID 15058197HCID 15058197, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 21583983Benzene ethyl acetateSolvent

Procedure

To a methanol solution (120 ml) of 1.600 g of 3-diphenylmethoxy-6-hydroxymethyl-1-isopropyl-4-pyridone is added 10.00 g of active manganese dioxide at room temperature, and the mixture is stirred for 5 hours, then at 50° C. for 1 hour. After insolubles are removed by filtration, the filtrate is condensed under reduced pressure and the residue is subjected to flash column chromatography on 100 g of Wako-Gel C-300 (manufactured by Wako Pure Chemical Industries, Ltd.) with an eluent of benzene-ethyl acetate (1:2) to perform separation and purification. The title compound (0.862 g) is obtained as colorless foam.

Workup

  1. waitat 50° C. for 1 hour
  2. customAfter insolubles are removed by filtration
  3. customcondensed under reduced pressure
  4. customseparation and purification

Sources & evidence

ORD record
ord-cf04029a74e242ae906653eba07b86ab
Source dataset
uspto-grants-1991_01
Patent number
US04988686

Reaction notes

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