Water → 4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

HRID 1836418Notes

Reaction equation

HRID 1836418 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[O: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.O>CO>[CH3:3][C:4]1[O: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

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 107561164-(5-Methyl-2-phenyl-4-oxazolyl)methoxybenzaldehyde

Product 1

HCID 110228074-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcoholYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (4.31 g) was gradually added to a solution of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (33.42 g) in methanol (150 ml)-tetrahydrofuran (30 ml) at 0° C. After the mixture was stirred at room temperature for 30 minutes, water was added to the reaction mixture followed by stirring for 1 hour. The precipitating crystals of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylalcohol (32.85 g; yield: 98%) were collected by filtration. Recrystallization from ethyl acetate-diethyl ether gave pale yellow crystals. Melting point: 128-129° C.

Workup

  1. stirringby stirring for 1 hour

Sources & evidence

ORD record
ord-9e052184d35f42449dc27a9dab5df390
Source dataset
uspto-grants-2004_08
Patent number
US06777435B1

Reaction notes

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