Hydrochloric Acid → 1-[(5R)-4,5-dihydro-5-phenyl-3-isoxazoyl]ethanone

HRID 1528550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528550
CN(C)[C:3]([C:5]1[CH2:9][C@H: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([C@@H: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

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 68744213(5R)-4,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazolecarboxamide2×HCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 687444941-[(5R)-4,5-dihydro-5-phenyl-3-isoxazoyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A solution of (5R)-4,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazole-carboxamide (i.e. the product of Example 12, Step D) (3.5 g, 16.0 mmol) in a mixture of tetrahydrofuran (5 mL) and toluene (10 mL) was cooled to −15° C., and methyl magnesium bromide (3.0M solution in tetrahydrofuran, 8.8 mL, 26.4 mmol) was added over 1 h at −15° C. Then the reaction mixture was poured over a mixture of 20 g of concentrated hydrochloric acid and 80 g of ice, and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (100 mL), and the combined extract was washed with brine (40 mL) and concentrated under reduced pressure to give 3.2 g of 1-[(5R)-4,5-dihydro-5-phenyl-3-isoxazoyl]ethanone.

Aufarbeitung

  1. customthe organic phase was separated
  2. extractionThe aqueous phase was extracted with ethyl acetate (100 mL)
  3. extractionthe combined extract
  4. washwas washed with brine (40 mL)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e9c064b0650c4a5896374cfc378bb1cc
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090604B2

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