Ethanol → HCID 23076357, compound

HRID 2221532Notes

Reaction equation

HRID 2221532 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:6][C:7]=1[CH:8]=[O:9].C(O)C.[BH4-].[Na+].O.[O:22]1[CH2:26]CC[CH2:23]1>>[CH3:23][O:22][CH2:26][O:1][CH2:2][C:3]1[N:4]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:6][C:7]=1[CH2:8][OH:9]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 230764914-Hydroxymethyl-2-phenyloxazole-5-carbaldehyde

Product 1

HCID 23076357HCID 23076357, compoundYield 76%

Procedure

To a solution of 4-hydroxymethyl-2-phenyloxazole-5-carbaldehyde (0.25 g) in tetrahydrofuran (5 mL)-ethanol (3 mL) was gradually added sodium borohydride (0.04 g) at 0° C. After stirring at room temperature for 1 hr, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give (4-methoxymethoxymethyl-2-phenyl-1,3-oxazol-5-yl)methanol as colorless crystals (0.19 g, yield 76%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 70-71° C.

Workup

  1. customat 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2c75e808451d458aa74943bf6c1af290
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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