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

HRID 1294176Notes

Reaction equation

HRID 1294176 reaction equation
[CH3:1][C:2]1[S: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:30]=[CH:29][C:18]([CH2:19][O:20][C:21]2[N:28]=[CH:27][CH:26]=[CH:25][C:22]=2[CH:23]=[O:24])=[CH:17][CH:16]=1.O1CCCC1.C(O)C.[BH4-].[Na+]>O>[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][O:20][C:21]2[C:22]([CH2:23][OH:24])=[CH:25][CH:26]=[CH:27][N:28]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 865915642-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]nicotinaldehyde

Product 1

HCID 68884317[2-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]-3-pyridyl]methanolYield 97.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-[4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]nicotinaldehyde (2.16 g), tetrahydrofuran (30 ml) and ethanol (30 mL) was added sodium borohydride (0.20 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, and dried with air to give crystals (2.12 g, 97%) of [2-[4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]-3-pyridyl]methanol. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 111-112° C.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. customdried with air

Sources & evidence

ORD record
ord-f079222da14e42ccb73be0aec47dfa26
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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