Sodium Bicarbonate → 1-(4-Fluorophenyl)-1-(4-methyl-5-oxazolyl)methanol

HRID 1458218Notes

Reaction equation

HRID 1458218 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[CH:7]=[O:8].[F:9][C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:7]([C:6]2[O:5][CH:4]=[N:3][C:2]=2[CH3:1])[OH:8])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 149205234-Methyl-1,3-oxazole-5-carbaldehydeHCID 178418676HCID 178418676, compound

Product 1

HCID 221018021-(4-Fluorophenyl)-1-(4-methyl-5-oxazolyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Methyl-5-oxazolecarbaldehyde (770 mg) in dry tetrahydrofuran (15 ml) was added dropwise to a stirred solution of 4-fluorophenyl magnesium bromide (1M solution in tetrahydrofuran, 7.3 ml) in tetrahydrofuran (30 ml) at -70° C. under an atmosphere of dry nitrogen. After 1 hour the mixture was allowed to warm to room temperature and was then poured into saturated aqueous sodium hydrogen carbonate. Extraction with ethyl acetate followed by flash chromatography gave the title compound. M.p. 102.5°-104° C.

Workup

  1. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-31931ccc9b7b47a88d3de4bc759119f4
Source dataset
uspto-grants-1998_12
Patent number
US05849921

Reaction notes

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