Ethanol → (3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxyphenyl)methanol

HRID 2221513Notes

Reaction equation

HRID 2221513 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH:16]=[O:17])[N:10]=1.C(O)C.[BH4-].[Na+].O>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][O:12][C:13]2[CH:14]=[C:15]([CH2:16][OH:17])[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[N:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 866057063-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzaldehyde

Product 1

HCID 69217094(3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxyphenyl)methanolYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzaldehyde (14.0 g) in tetrahydrofuran (100 mL)-ethanol (30 mL) was gradually added sodium borohydride (1.69 g) at 0° C. After stirring at room temperature for 2 hrs., water was added to the reaction mixture and the precipitated crystals were collected by filtration to give (3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxyphenyl)methanol as pale-yellow crystals (12.87 g, yield 91%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 145-146° C.

Workup

  1. customat 0° C
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-205ecc69add94c17b8ee41d28397c54d
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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