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

HRID 1294205Notes

Reaction equation

HRID 1294205 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:21])=[C:9]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][N:14]=2)[N:10]=1.O1CCCC1.C(O)C.[BH4-].[Na+]>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:21])=[C:9]([CH2:11][O:12][C:13]2[N:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:19][CH:20]=2)[N:10]=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

To a mixture of 6-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]nicotinaldehyde (3.10 g), tetrahydrofuran (50 ml) and ethanol (50 mL) was added sodium borohydride (0.41 g) at room temperature and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added water 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 crystals (2.86 g, 92%) of [6-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-pyridyl]methanol. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 120-121° C.

Workup

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

Sources & evidence

ORD record
ord-1b2da914e29c4802b958a5f746c0c8de
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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