Sodium Bicarbonate → 1-(4-Methyl-5-oxazolyl)-1-phenylmethanol

HRID 727250Notes

Reaction equation

HRID 727250 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[CH:7]=[O:8].[C:9]1([Li])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 149205234-Methyl-1,3-oxazole-5-carbaldehydeHCID 178506676HCID 178506676, compound

Product 1

HCID 103134521-(4-Methyl-5-oxazolyl)-1-phenylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Methyl -5-oxazolecarbaldehyde (600 m g) in dry tetrahydrofuran (10 ml) was added dropwise to a stirred solution of phenyllithium (2.0M solution in cyclohexane and diethyl ether, 2.8 ml) in tetrahydrofuran (20 ml) at -70° C. under an atmosphere of dry nitrogen. After 1 hour the mixture was allowed to warm to room temperature. After a further 1 hour saturated aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The product was purified by flash chromatography to yield the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-2b3b0e2ba3bc4efe81419f52aea203b9
Source dataset
uspto-grants-1998_01
Patent number
US05712299

Reaction notes

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