Bis(trimethylsilylmethyl) sulfoxide → 5-(4'-Chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione

HRID 40473노트

반응식

HRID 40473 반응식
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:17])[CH:15]=[CH:14][C:13]3=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.C[Si]([CH2:27][S:28]([CH2:30][Si](C)(C)C)=O)(C)C>CN1CCCN(C)C1=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[CH:7]=[CH:8][C:9]([CH2:19][CH3:20])=[C:10]([CH:12]3[C:16](=[O:17])[CH:15]4[CH2:27][S:28][CH2:30][CH:14]4[C:13]3=[O:18])[CH:11]=2)=[CH:21][CH:22]=1

참가 물질

4

반응물 2

HCID 13694173Bis(trimethylsilylmethyl) sulfoxideHCID 497657352-(4'-Chloro-4-ethylbiphenyl-3-yl)cyclopent-4-ene-1,3-dione

생성물 1

HCID 497657365-(4'-Chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione

시약·촉매·용매 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-용매

반응 조건

온도
100 °C

실험 절차

A suspension of 2-(4′-chloro-4-ethylbiphen-3-yl)cyclopent-4-ene-1,3-dione (0.200 g, 0.65 mmol) and crude bis(trimethylsilylmethyl)sulphoxide (0.406 g, 0.97 mmol) in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (3 ml) is heated at 100° C. for 20 minutes under microwave irradiation. The reaction mixture is then partitioned between diethylether and distilled water, and the organic phase is washed with water (×2) then brine. After drying over magnesium sulfate the crude mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is purified by preparative reverse phase HPLC to afford 5-(4′-chloro-4-ethylbiphenyl-3-yl)-tetrahydrocyclopenta[c]thiophene-4,6-dione.

후처리

  1. customThe reaction mixture is then partitioned between diethylether
  2. distillationdistilled water
  3. washthe organic phase is washed with water (×2)
  4. dry with materialAfter drying over magnesium sulfate the crude mixture
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue is purified by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-f1dd7b843eee4992a79052391d8a5eed
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530388B2

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