Methanol → 2-(5-Methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-methanol

HRID 1295225Notes

Reaction equation

HRID 1295225 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:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][N:16]=1.CO.[BH4-].[Na+].O>O1CCCC1>[CH3:1][C:2]1[O: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:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 185461556-(5-Methyl-2-phenyl-4-oxazolylmethoxy)nicotinaldehyde

Product 1

HCID 178328032-(5-Methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-carbaldehyde (13.0 g) in tetrahydrofuran (150 ml)-methanol (10 ml) was gradually added sodium borohydride (835 mg) at 0° C. After stirring for 30 min., water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-methanol as crystals. The crystals were recrystallized from acetone-isopropyl ether to give colorless prism crystals (12.4 g, yield 95%). melting point: 121–122° C.

Workup

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

Sources & evidence

ORD record
ord-0b5bae9a00a04982a3f60f90f6b188e4
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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