Methanol → 3,5-Dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

HRID 2299756Notes

Reaction equation

HRID 2299756 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:27][CH3:28])[C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20])[CH:8]=[O:9].CO.O>O1CCCC1>[CH3:28][O:27][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([O:4][CH3:3])[C:12]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20])[CH2:8][OH:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 223445793,5-Dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde

Product 1

HCID 536741583,5-Dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcoholYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (540 mg) was added to a solution of 3,5-dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (10.0 g) in tetrahydrofuran (70 ml)-methanol (30 ml) at 0° C. After stirring for 1 hour, the reaction mixture was poured into water to give 3,5-dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol (9.25 g, yield 92%) as crystals. Recrystallization from ethyl acetate-hexane gave colorless prisms. m.p. 113-114° C.

Sources & evidence

ORD record
ord-ea3ec0d84f2449dc93b40c6cbe8f00cf
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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