Hydrochloric Acid → (4-Methyloxazol-5-yl)(phenyl)methanone

HRID 875187

Reaction equation

HRID 875187 reaction equation
[Cl-].[Li+].CON(C)[C:6]([C:8]1[O:12][CH:11]=[N:10][C:9]=1[CH3:13])=[O:7].[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl>C(OCC)C.[Cu]I.O>[CH3:13][C:9]1[N:10]=[CH:11][O:12][C:8]=1[C:6]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 433294Lithium ChlorideHCID 18925369N-Methoxy-N,4-dimethyloxazole-5-carboxamideHCID 178418255HCID 178418255, compound

Product 1

HCID 53876795(4-Methyloxazol-5-yl)(phenyl)methanoneYield 38.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of lithium chloride (0.77 g, 18.2 mmol) and copper(I) iodide (0.087 g, 0.45 mmol) was added diethylether (30 ml). After stirring for 5 minutes a solution of N-methoxy-N,4-dimethyl-1,3-oxazole-5-carboxamide (2.58 g, 15.16 mmol) in diethylether (30 ml) was added followed by the slow addition of phenylmagnesium bromide (4.12 g, 22.74 mmol). After stirring for 20 hours at room temperature 1N HCl (20 mL) and water (30 mL) were added. The mixture was extracted with dichloromethane, the organic layer was washed with water, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude material on silica gel afforded (4-methyl-1,3-oxazol-5-yl)(phenyl)methanone (1.08 g, 30%)

Workup

  1. additionwas added
  2. additionwere added
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude material on silica gel

Sources & evidence

ORD record
ord-12f6ae5917cc4649b0dca1968c1da7a9
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Linked notes

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