Chloro(diphenyl)silane → 2-Benzyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 30295

반응식

HRID 30295 반응식
[Cl-].[Cl-].[Cl-].[In+3].Cl[SiH](C1C=CC=CC=1)C1C=CC=CC=1.[CH2:19]([N:26]1[CH2:33][CH:32]2[CH:28]([CH:29](O)[C:30]3[CH:36]=[CH:35][S:34][C:31]=32)[CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClC(Cl)C>[CH2:19]([N:26]1[CH2:33][CH:32]2[CH:28]([CH2:29][C:30]3[CH:36]=[CH:35][S:34][C:31]=32)[CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

참가 물질

5

반응물 3

HCID 74206Chloro(diphenyl)silaneHCID 159675indium(III)chlorideHCID 1317270502-Benzyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalen-7-ol

생성물 1

HCID 1317270492-Benzyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene수율 57%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

반응 조건

온도
60 °C

실험 절차

Indiumtrichloride (973 mg, 4.40 mmol) and chlorodiphenylsilane (2888 mg, 13.20 mmol) were added to a solution of the product from step f) (1192 mg, 4.40 mmol) in 20 mL of dichloroethane. The reaction mixture was heated at 60° C. overnight and then was cooled to room temperature and quenched with saturated NaHCO3 (50 ml). The reaction mixture was extracted with ethylacetate (2×50 mL). The combined organic extracts were washed with brine (50 ml), dried with MgSO4 and solvent evaporated in vacuo to afford the subtitle compound (638 mg, yield: 57%) that was used without further purification. MS calculated C16H17NS+H: 256, observed: 256.

후처리

  1. temperaturewas cooled to room temperature
  2. customquenched with saturated NaHCO3 (50 ml)
  3. extractionThe reaction mixture was extracted with ethylacetate (2×50 mL)
  4. washThe combined organic extracts were washed with brine (50 ml)
  5. dry with materialdried with MgSO4 and solvent
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-e1aa197d0bd24dc7b74e830b3a5cd79a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423056B2

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