Ethanol → HCID 69217028, compound

HRID 2221647Notes

Reaction equation

HRID 2221647 reaction equation
[CH:1]([C:3]1[CH:24]=[CH:23][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[O:12][C:13]=2[CH3:14])=[C:5]([O:25][CH3:26])[CH:4]=1)=[O:2].C(O)C.[BH4-].[Na+].O>O1CCCC1>[OH:2][CH2:1][C:3]1[CH:24]=[CH:23][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[C:18]#[N:19])[O:12][C:13]=2[CH3:14])=[C:5]([O:25][CH3:26])[CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86605742HCID 86605742, compound

Product 1

HCID 69217028HCID 69217028, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzonitrile (20.0 g) in tetrahydrofuran (300 mL)-ethanol (30 mL) was gradually added sodium borohydride (1.09 g) at 0° C. After stirring at room temperature for 1 hr, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 3-{4-[(4-hydroxymethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzonitrile as colorless crystals (19.2 g, yield 96%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 113-115° C.

Workup

  1. customat 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-17f1f0e3b6284663ad2ba98a9e508fc0
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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