Chloro(diphenyl)silane → 2-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 1013364

반응식

HRID 1013364 반응식
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH:11](O)[C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[SiH](C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>ClC(Cl)C.CCOC(C)=O>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][C:12]3[C:18]([Br:19])=[C:17]([Br:20])[S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 74206Chloro(diphenyl)silaneHCID 516892Sodium BicarbonateHCID 1317270292-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalen-7-ol

생성물 1

HCID 1317270302-Benzyl-5,6-dibromo-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

The product from step f) (300 mg, 0.69 mmol) in dichloroethane (2.6 ml) was treated with InCl3 (153 mg, 0.69 mmol) and chlorodiphenylsilane (457 mg, 2.08 mmol). The contents were heated to 60° C. for 16 hours. The reaction mixture was cooled to 22° C., poured into sat. NaHCO3 and diluted with EtOAc (75 ml); producing a white emulsion. The emulsion was passed through celite and the organic layer was separated, washed with brine (25 ml) and dried (MgSO4). The crude product was dissolved in 7:3 hexanes:EtOAc and passed through a plug of silica gel to give the subtitle compound. MS calculated for C16H15Br2NS+H 414, observed 412, 414, 416.

후처리

  1. temperatureThe reaction mixture was cooled to 22° C.
  2. customproducing a white emulsion
  3. customthe organic layer was separated
  4. washwashed with brine (25 ml)
  5. dry with materialdried (MgSO4)
  6. dissolutionThe crude product was dissolved in 7:3 hexanes

출처 및 근거

ORD 기록
ord-d93270e23f514652841b6f02b2a5de08
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981919B2

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