Potassium Carbonate → 5-(5,5-Dimethyl-4,5-dihydroisoxazol-3-ylsulfanylmethyl)-3-methoxy-isoxazole

HRID 1192957

反応式

HRID 1192957 の反応式
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=1.NC(N)=S.C[S:15]([C:18]1[CH2:22][C:21]([CH3:24])([CH3:23])[O:20][N:19]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:23][C:21]1([CH3:24])[O:20][N:19]=[C:18]([S:15][CH2:2][C:3]2[O:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=2)[CH2:22]1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 108454055-(Bromomethyl)-3-methoxy-1,2-oxazoleHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazoline

生成物 1

HCID 597395995-(5,5-Dimethyl-4,5-dihydroisoxazol-3-ylsulfanylmethyl)-3-methoxy-isoxazole収率 45%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

5-Bromomethyl-3-methoxy-isoxazole (1.22 g, 6.35 mmol) was dissolved in ethanol (30 ml) and thiourea (484 mg, 6.4 mmol) was added. The mixture was stirred at room temperature until the solids were dissolved. 3-Methanesulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (1.08 g, 6.4 mmol) and potassium carbonate (880 mg, 6.4 mmol) were added and the mixture was heated under reflux for 1 hour. The solids were removed by filtration and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product as colourless oil (0.69 g, 45% yield over 3 steps).

後処理

  1. dissolutionwere dissolved
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-1b84df4719be4e77bd721b89be15f453
出典データセット
uspto-grants-2014_03
特許番号
US08680290B2

関連ノート

読み込み中…