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

HRID 1294115Notes

Reaction equation

HRID 1294115 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 crystals of 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine-5-methanol. Recrystallization from acetone-isopropyl ether gave 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-9c7d0e93be154c6abdad9a0afe0188dc
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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