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

HRID 350010Notes

Reaction equation

HRID 350010 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.O1CCCC1.Cl>O.CO>[CH3:3][C:4]1[S:8][C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][OH:22])=[CH:23][CH:24]=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

Sodium borohydride (0.38 g) was added to a mixture of 4-(5-methyl-2-phenyl-4-thiazolylmethoxy)benzaldehyde (6.00 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 air-dried to obtain crystals of 4-(5-methyl-2-phenyl-4-thiazolylmethoxy)benzyl alcohol (5.68 g, yield 94%). This was recrystallized from ethyl acetate-hexane to obtain colorless prisms. Melting point: 94–95° C.

Workup

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

Sources & evidence

ORD record
ord-bb8633b14cda4cf0b891ed812e253032
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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