Ethanol → HCID 69215991, compound

HRID 2221570Notes

Reaction equation

HRID 2221570 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:16][C:17]=1[CH3:18])[CH:6]=[O:7].C(O)C.[BH4-].[Na+].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:16][C:17]=1[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86605715HCID 86605715, compound

Product 1

HCID 69215991HCID 69215991, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-4-[(5-methyl-2-phenyl-1,3-thiazol-4-yl)methoxy]benzaldehyde (1.15 g) in tetrahydrofuran (10 mL)-ethanol (10 mL) was gradually added sodium borohydride (0.13 g) at room temperature. After stirring the reaction mixture for 2 hrs, water was added, and the precipitated crystals were collected by filtration to give {3-methoxy-4-[(5-methyl-2-phenyl-1,3-thiazol-4-yl)methoxy]phenyl}methanol as colorless crystals (1.05 g, yield 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 134-135° C.

Workup

  1. customat room temperature
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-74d410d2fa3f4760be68e0eba74b00bb
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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