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

HRID 1528550노트

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HRID 1528550 반응식
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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 68744213(5R)-4,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazolecarboxamide2회HCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-15 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9c064b0650c4a5896374cfc378bb1cc
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090604B2

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