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

HRID 1458217Notes

Reaction equation

HRID 1458217 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 mg) 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. M.p. 79°-81° C.

Workup

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

Sources & evidence

ORD record
ord-e3f718e7d8ef4d708180674db2d2fed9
Source dataset
uspto-grants-1998_12
Patent number
US05849921

Reaction notes

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