Hydrochloric Acid → 1-(4,5-Dihydro-5-phenyl-3-isoxazoyl)ethanone

HRID 238687Notes

Reaction equation

HRID 238687 reaction equation
CN(C)[C:3]([C:5]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][N:6]=1)=[O:4].C[Mg]Br.Cl.[O:21]1CC[CH2:23][CH2:22]1>C1(C)C=CC=CC=1>[C:10]1([CH:8]2[O:7][N:6]=[C:5]([C:3]([C:22](=[O:21])[CH3:23])=[O:4])[CH2:9]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 672359144,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazolecarboxamide2×HCID 178418573HCID 178418573, compound

Product 1

HCID 687444721-(4,5-Dihydro-5-phenyl-3-isoxazoyl)ethanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazolecarboxamide (i.e. the product of Example 12, Step A) (17 g, 78.0 mmol) in a mixture of tetrahydrofuran (20 mL) and toluene (80 mL) was added methyl magnesium bromide (3.0 M solution in tetrahydrofuran, 28 mL, 84 mmol) over 1 h, while keeping the reaction temperature between −10 and −15° C. The reaction mixture was poured over a mixture of concentrated hydrochloric acid (20 g) and ice (80 g), and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (100 mL), and the combined organic extracts were washed with brine (40 mL) and concentrated under reduced pressure to give 14.4 g of 1-(4,5-dihydro-5-phenyl-3-isoxazoyl)ethanone as a light yellow oil.

Workup

  1. customthe reaction temperature between −10 and −15° C
  2. customthe organic phase was separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (100 mL)
  4. washthe combined organic extracts were washed with brine (40 mL)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aad29d5359bd4489ad966e103442f6df
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Reaction notes

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