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

HRID 1192957

반응식

HRID 1192957 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1b84df4719be4e77bd721b89be15f453
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680290B2

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