Methanol → HCID 17861351, compound

HRID 349953Notes

Reaction equation

HRID 349953 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20].O1CCCC1.CO>O>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][C:6]=1[O:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 21224416HCID 21224416, compound

Product 1

HCID 17861351HCID 17861351, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (0.378 g) was added to a mixture of 4-methoxy-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzaldehyde (3.23 g), tetrahydrofuran (15 ml) and methanol (15 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 with anhydrous magnesium sulfate and concentrated to obtain crystals of 4-methoxy-3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol. This was recrystallized from tetrahydrofuran-hexane to obtain pale yellow plates (3.22 g, 99%). Melting point: 144–145° C.

Workup

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

Sources & evidence

ORD record
ord-bfea5ebfb4a344d09e1860eaea83e24c
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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