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

HRID 2096021ノート

反応式

HRID 2096021 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 68744213(5R)-4,5-dihydro-N,N-dimethyl-5-phenyl-3-isoxazolecarboxamide2 回HCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-15 °C

実験手順

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 (3.0 M 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.

後処理

  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

出典と根拠

ORDレコード
ord-06abd5c37789474e891ee717360e2a08
出典データセット
uspto-grants-2013_05
特許番号
US08449898B2

反応ノート

読み込み中…