Methanol → 5-[[4-[[(4E)-6-hydroxy-2,5,7,8-tetramethyl-4-phenylmethoxyimino-3H-chromen-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

HRID 1030368Notes

Reaction equation

HRID 1030368 reaction equation
[OH:1][C:2]1[C:3]([CH3:32])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][C:5]2=O.Cl.[CH2:34]([O:41][NH2:42])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CO.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH2:34]([O:41]/[N:42]=[C:5]1\[CH2:6][C:7]([CH2:15][O:16][C:17]2[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=2)([CH3:14])[O:8][C:9]2[C:4]\1=[C:3]([CH3:32])[C:2]([OH:1])=[C:11]([CH3:12])[C:10]=2[CH3:13])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 102312Benzyloxyamine hydrochlorideHCID 98252415-[4-(6-Hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Product 1

HCID 884914025-[[4-[[(4E)-6-hydroxy-2,5,7,8-tetramethyl-4-phenylmethoxyimino-3H-chromen-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1 g of 5-[4-(6-hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Example 22 of copending U.S. Ser. No. 644,996), 1.2 g of benzyloxylamine hydrochloride and 10 g of methanol was allowed to stand for 7 days at room temperature. At the end of this time, ethyl acetate and an aqueous solution of potassium carbonate were added. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography eluted with a 3:1 by volume mixture of hexane and ethyl acetate, to give the title compound, softening at 64°-69° C.

Workup

  1. customprepared
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography
  6. washeluted with a 3:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-90f4cacb967d443abd0ccf76ab52ebeb
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

Loading…