Methanol → HCID 68884893, compound

HRID 1294112Notes

Reaction equation

HRID 1294112 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:32]=[CH:31][C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([C:27](OC)=[O:28])[CH:24]=[N:25][CH:26]=2)=[CH:17][CH:16]=1.[BH4-].[Na+].O1CCCC1.CO>O>[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:32]=[CH:31][C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH2:27][OH:28])[CH:24]=[N:25][CH:26]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 68884954HCID 68884954, compound

Product 1

HCID 68884893HCID 68884893, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of methyl 5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridinecarboxylate (2.09 g), sodium tetrahydroborate (0.93 g) and tetrahydrofuran (100 mL) was dropwise added methanol (10 mL) at 50° C., and the mixture was stirred at 50° C. for 1 hr. 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 (1.85 g, 94%) of [5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 128-130° C.

Workup

  1. customat 50° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e89a1c470cc54fef9dd0b49a163fcae6
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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