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

HRID 2221522Notes

Reaction equation

HRID 2221522 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:20]=[CH:19][C:16]([CH:17]=[O:18])=[C:15]([O:21][CH3:22])[CH:14]=2)[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:20]=[CH:19][C:16]([CH2:17][OH:18])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 866057074-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxybenzaldehyde

Product 1

HCID 69217781(4-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxyphenyl)methanolYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxybenzaldehyde (3.00 g) in tetrahydrofuran (30 mL)-ethanol (10 mL) was gradually added sodium borohydride (0.36 g) at 0° C. After stirring at room temperature for 1 hr., water was added to the reaction mixture and the precipitated crystals were collected by filtration to give (4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-2-methoxyphenyl)methanol as colorless crystals (2.91 g, yield 96%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 117-118° C.

Workup

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

Sources & evidence

ORD record
ord-70e102d7b9fa4bb59a2d804007b1c79f
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…