HCID 15159550, compound → HCID 15159551, compound

HRID 704663Notes

Reaction equation

HRID 704663 reaction equation
[CH3:1][O:2][C:3]1[CH:50]=[CH:49][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:36]=[CH:37][C:38]=2[O:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[CH2:12][N:13]2[C:18]([CH2:19][OH:20])=[CH:17][C:16](=[O:21])[C:15]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:14]2)=[CH:5][CH:4]=1>[O-2].[O-2].[Mn+4].ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:36]=[CH:37][C:38]=2[O:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)[CH2:12][N:13]2[C:18]([CH:19]=[O:20])=[CH:17][C:16](=[O:21])[C:15]([O:22][CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14]2)=[CH:49][CH:50]=1

Participants

4

Reactant 1

HCID 15159550HCID 15159550, compound

Product 1

HCID 15159551HCID 15159551, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (210 ml) of 1-[3,4-bis(p-methoxybenzyloxy)benzyl]-3-diphenylmethoxy-6-hydroxymethyl-4-pyridone (0.462 g) is added active manganese dioxide (2.40 g), and the mixture is stirred at room temperature for 20 minutes. Insolubles are removed by filtration, the filtrate is subjected to flash column chromatography on 50 g of Wako-Gel C-300 (manufactured by Wako Pure Chemical Industries, Ltd.) with an eluent of chloroform-methanol (20:1) to perform separation and purification. The title compound (0.264 g) is thus obtained as colorless crystal.

Workup

  1. customInsolubles are removed by filtration
  2. customseparation and purification

Sources & evidence

ORD record
ord-3164b86616c9401393a4ad6f964fd611
Source dataset
uspto-grants-1991_01
Patent number
US04988686

Reaction notes

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