Acetic Acid → HCID 13236231, compound

HRID 1462924Notes

Reaction equation

HRID 1462924 reaction equation
[CH3:1][C:2]1([CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[BH4-].[Na+].C(O)(=O)C.O>CO>[OH:8][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:2]1([CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][CH:16]2[S:20][C:19](=[O:21])[NH:18][C:17]2=[O:22])=[CH:13][CH:12]=1)[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 15591801HCID 15591801, compound

Product 1

HCID 13236231HCID 13236231, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-[4-(1-methyl-2-oxocyclohexylmethoxy)benzyl]thiazolidine-2,4-dione (5.2 g) in methanol (50 ml), sodium borohydride (0.757 g) was added under ice cooling. The mixture was stirred with ice cooling for 30 minutes, then acetic acid (2 ml) was added. The mixture was poured into water and extracted with benzene. The extract was washed with water and dried (MgSO4). The benzene was distilled off, and the oily residue was subjected to silica gel (100 g) column chromatography. From the benzene-acetone (10:1, v/v) eluate fractions, 5-[4-(2-hydroxy-1-methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione was obtained as a powder (4.2 g, 80.8%). m.p. 101°-103° C. The thus-obtained powder was a mixture of two isomers different in the configuration of the hydroxyl group on the cyclohexane ring.

Workup

  1. additionwas added under ice cooling
  2. extractionextracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationThe benzene was distilled off

Sources & evidence

ORD record
ord-89e92884104142e6ba9a8791dcc3d66a
Source dataset
uspto-grants-1984_07
Patent number
US04461902

Reaction notes

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