Ethanol → HCID 69216007, compound

HRID 2221568Notes

Reaction equation

HRID 2221568 reaction equation
[CH:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:27][CH3:28])[CH:4]=1)=[O:2].C(O)C.[BH4-].[Na+].O>O1CCCC1>[OH:2][CH2:1][C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:27][CH3:28])[CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86605714HCID 86605714, compound

Product 1

HCID 69216007HCID 69216007, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate (0.92 g) in tetrahydrofuran (20 mL)-ethanol (10 mL) was gradually added sodium borohydride (0.09 g) at room temperature. After stirring the reaction mixture for 1 hr, water was added, and the precipitated crystals were collected by filtration to give methyl 4-{4-[(4-hydroxymethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzoate as colorless crystals (0.83 g, yield 90%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 170-171° C.

Workup

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

Sources & evidence

ORD record
ord-e77d885ee0ef4ff191bd89dc1f9d8ded
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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