Ethanol → [2-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]methanol

HRID 1294219Notes

Reaction equation

HRID 1294219 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[N:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH:24]=[O:25])[O:17][N:16]=1.O1CCCC1.C(O)C.[BH4-].[Na+]>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[C:23]([CH2:24][OH:25])=[CH:26][CH:27]=[CH:28][N:29]=2)[O:17][N:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 865915712-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinaldehyde

Product 1

HCID 68885895[2-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]methanolYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinaldehyde (1.64 g), tetrahydrofuran (20 ml) and ethanol (20 mL) was added sodium borohydride (80 mg) at 0° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the precipitated crystals were collected by filtration and recrystallized from ethyl acetate-isopropyl ether to give colorless needle crystals (1.50 g, 91%) of [2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]methanol. melting point: 136-137° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customrecrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-14c25e13263c45c2afa18061ff6dbfcb
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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