Ethanol → [4-[(2-Phenyl-5-propyl-4-oxazolyl)methoxy]phenyl]methanol

HRID 1294164Notes

Reaction equation

HRID 1294164 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH2:22][CH2:23][CH3:24])=[C:10]([CH2:12][O:13][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.C(O)C.[BH4-].[Na+]>O>[C:1]1([C:7]2[O:8][C:9]([CH2:22][CH2:23][CH3:24])=[C:10]([CH2:12][O:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:20][CH:21]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 865915624-[(2-Phenyl-5-propyl-4-oxazolyl)methoxy]benzaldehyde

Product 1

HCID 68886296[4-[(2-Phenyl-5-propyl-4-oxazolyl)methoxy]phenyl]methanolYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]benzaldehyde (2.40 g), tetrahydrofuran (30 ml) and ethanol (10 mL) was added sodium borohydride (0.28 g) at room temperature and the mixture was stirred at room temperature for 1 hr. To, the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (1.60 g, 66%) of [4-[(2-phenyl-5-propyl-4-oxazolyl)methoxy]phenyl]methanol from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 79-80° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-682f072737cb4c5cb653b2182126b4ac
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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