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2-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin → 2-Cyano-6,11-dihydro-11-ethylidenedibenz[b,e]oxepin

HRID 894221
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HRID 894221 반응식
[C:1]([Li])(C)(C)[CH3:2].[C:6]([C:8]1[CH:23]=[CH:22][C:11]2[O:12][CH2:13][C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[C:16](=O)[C:10]=2[CH:9]=1)#[N:7]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1.CCCCCC>[C:6]([C:8]1[CH:23]=[CH:22][C:11]2[O:12][CH2:13][C:14]3[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=3[C:16](=[CH:1][CH3:2])[C:10]=2[CH:9]=1)#[N:7]
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참가 물질

6

반응물 2

HCID 124468252-Cyano-6,11-dihydro-11-oxodibenz[b,e]oxepinHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 536734252-Cyano-6,11-dihydro-11-ethylidenedibenz[b,e]oxepin

시약·촉매·용매 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)촉매HCID 8028Tetrahydrofuran용매2회
HCID 8058
Hexane
용매

실험 절차

Suspent 23.6 gm of ethyl triphenylphosphonium bromide in 200 ml of dry tetrahydrofuran add dropwise 2.4 ml of t-butyllithium in hexane with stirring at room temperature under a nitrogen atmosphere. Continue stirring for 3 hours and then cool to -70° C. in a dry ice bath. Add 10 gm. of 2-cyano-6,11-dihydro-11-oxodibenz[b,e]oxepin in 75 ml of dry tetrahydrofuran dropwise over 30 minutes. Continue stirring at -70° C. for 30 minutes, warm to room temperature and continue stirring overnight under a nitrogen atmosphere. Pour the mixture into 400 ml. of ether, filter and wash the filtrate with saturated aqueous sodium chloride solution. Dry over anhydrous magnesium sulfate and strip to dryness. Chromatograph the residue over silica gel, eluting with 5% ethyl acetate in hexane to obtain the final product (5.73 gm).

후처리

  1. stirringContinue stirring for 3 hours
  2. temperaturecool to -70° C. in a dry ice bath
  3. additionAdd 10 gm
  4. stirringContinue stirring at -70° C. for 30 minutes
  5. temperaturewarm to room temperature
  6. stirringcontinue stirring overnight under a nitrogen atmosphere
  7. additionPour the mixture into 400 ml
  8. filtrationof ether, filter
  9. washwash the filtrate with saturated aqueous sodium chloride solution
  10. dry with materialDry over anhydrous magnesium sulfate and strip to dryness
  11. washChromatograph the residue over silica gel, eluting with 5% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-080c06b0d92e4e499148774c4771fca7
출처 데이터셋
uspto-grants-1981_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04282365

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