Hydrochloric Acid → 4-(5-Methyl-2-phenyl-4-thiazolylmethoxy)benzyl alcohol

HRID 1294124Notes

Reaction equation

HRID 1294124 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.O1CCCC1.[BH4-].[Na+].Cl>O.CO>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 230250854-(5-Methyl-2-phenyl-4-thiazolylmethoxy)benzaldehyde

Product 1

HCID 688862694-(5-Methyl-2-phenyl-4-thiazolylmethoxy)benzyl alcoholYield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzaldehyde (6.00 g), tetrahydrofuran (30 ml) and methanol (20 mL) was added sodium borohydride (0.38 g) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Dilute hydrochloric acid and water were added to acidify the reaction mixture, and the precipitated solid was collected by filtration, and dried with air to give crystals (5.68 g, 94%) of [4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]phenyl]methanol. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 94-95° C.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated solid was collected by filtration
  3. customdried with air

Sources & evidence

ORD record
ord-242f924ace3d4ade805bb10fba084c43
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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