Hydrochloric Acid → 4-(2-Phenyl-4-thiazolylmethoxy)benzyl alcohol

HRID 350007Notes

Reaction equation

HRID 350007 reaction equation
[BH4-].[Na+].[C:3]1([C:9]2[S:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=3)[N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1CCCC1.Cl>O.CO>[C:3]1([C:9]2[S:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:22][CH:23]=3)[N:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 105179614-(2-Phenyl-4-thiazolylmethoxy)benzaldehyde

Product 1

HCID 688882164-(2-Phenyl-4-thiazolylmethoxy)benzyl alcoholYield 90.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (0.45 g) was added to a mixture of 4-(2-phenyl-4-thiazolylmethoxy)benzaldehyde (6.35 g), tetrahydrofuran (30 ml) and methanol (20 ml) under ice-cooling, which was stirred at room temperature for 30 minutes. The reaction mixture was neutralized with dilute hydrochloric acid and water to give a precipitate, which was collected by filtration and then air-dried to obtain crystals of 4-(2-phenyl-4-thiazolylmethoxy)benzyl alcohol (5.76 g, yield 90%). This was recrystallized from ethyl acetate-hexane to obtain colorless needles. Melting point: 145–146° C.

Workup

  1. temperaturecooling
  2. customto give a precipitate, which
  3. filtrationwas collected by filtration
  4. customair-dried

Sources & evidence

ORD record
ord-654d4623bb144946b801621b4165af79
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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