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

HRID 349981Notes

Reaction equation

HRID 349981 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][N:18]=1.CO.O>O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[N:18]=[CH:19][C:20]([CH2:21][OH:22])=[CH:23][CH:24]=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

Sodium borohydride (835 mg) was added gradually to a solution of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)nicotinaldehyde (13.0 g) in tetrahydrofuran (150 ml)-methanol (10 ml) at 0° C. After stirring for 30 minutes, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to obtain crystals of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethanol. This was recrystallized from acetone-isopropyl ether to obtain colorless prism crystals (12.4 g, yield 95%). Melting point: 121–122° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5e77edf7409d4ba7abf56b57a06a2d48
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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