Ethanol → 6-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethanol

HRID 349983Notes

Reaction equation

HRID 349983 reaction equation
[BH4-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[O:9][C:10]([CH3:23])=[C:11]([CH2:13][O:14][C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][N:16]=2)[N:12]=1.O1CCCC1.C(O)C>O>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[C:8]1[O:9][C:10]([CH3:23])=[C:11]([CH2:13][O:14][C:15]2[N:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:21][CH:22]=2)[N:12]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 865915676-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]nicotinaldehyde

Product 1

HCID 688864106-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethanolYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (410 mg) was added to a mixture of 6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]nicotinaldehyde (3.10 g), tetrahydrofuran (50 ml) and ethanol (50 mL) at room temperature, which was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated to obtain 6-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-pyridylmethanol (2.86 g, yield 92%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 120–121° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8d84bfa1fc124ca2bbb0ab24ae5e332f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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