Water → 5-(4-Fluorophenyl)-2-oxazolemethanol

HRID 271300Notes

Reaction equation

HRID 271300 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([CH:15]=[O:16])=[N:12][CH:11]=2)=[CH:6][CH:5]=1.O>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][C:13]([CH2:15][OH:16])=[N:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 83383390HCID 83383390, compound

Product 1

HCID 435587275-(4-Fluorophenyl)-2-oxazolemethanolYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (138 mg, 3.6 mmol) was added to a solution of 5-(4-fluorophenyl)-1,3-oxazole-2-carbaldehyde (0.58 g, 3.03 mmol) in methanol (10 ml). The mixture was stirred at room temperature for 2 hours, then poured into water (50 ml), extracted with DCM (30 ml), washed with brine (20 ml), dried over MgSO4 and concentrated in vacuo to afford 460 mg (79%) of the title compound: δH (360 MHz, CDCl3) 2.57 (1H, m), 4.79 (2H, d, J 5.5) 7.12 (2H, t, J 8.5), 7.24 (1H, s), 7.60-7.64 (2H, m); m/z (ES+) 194 (MH+).

Workup

  1. extractionextracted with DCM (30 ml)
  2. washwashed with brine (20 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3518801224604c3c8acd940695d5e374
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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