Methanol → 4-[5-Methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyl alcohol

HRID 1294221Notes

Reaction equation

HRID 1294221 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.O1CCCC1.CO.[BH4-].[Na+]>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][OH:24])=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 185461594-[5-Methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzaldehyde

Product 1

HCID 688833594-[5-Methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyl alcoholYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzaldehyde (6.00 g), tetrahydrofuran (80 mL) and methanol (20 mL) was gradually added sodium borohydride (330 mg) at room temperature. After stirring for 30 min., water was added to the reaction mixture, and the precipitated crystals were collected by filtration and recrystallized from acetone-methanol to give colorless prism crystals (5.76 g, 95%) of 4-[5-methyl-2-(2-naphthyl)-4-oxazolylmethoxy]benzyl alcohol. melting point: 181-182° C.

Workup

  1. customat room temperature
  2. filtrationthe precipitated crystals were collected by filtration
  3. customrecrystallized from acetone-methanol

Sources & evidence

ORD record
ord-81a421e52c1a488eaaff4402bbab01ec
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…