Ammonium Chloride → HCID 86218651, 화합물

HRID 590508

반응식

HRID 590508 반응식
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:10])[CH2:7][CH2:8][CH2:9][C:2]1=2.[CH:11]([Mg]Cl)=[CH2:12].[Cl-].[NH4+]>C(OCC)C>[CH:11]([C:6]1([OH:10])[C:3]2[CH:4]=[CH:5][S:1][C:2]=2[CH2:9][CH2:8][CH2:7]1)=[CH2:12]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 178461836HCID 178461836, 화합물

생성물 1

HCID 86218651HCID 86218651, 화합물

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-30 °C

실험 절차

6,7-Dihydrobenzo[b]thiophen-4(5H)-one (8.48 g, 56 mmol) was dissolved in anhydrous diethyl ether (200 mL) and the solution was cooled to −30° C. Vinyl magnesium chloride (60 mL, 1.6 M solution in THF, 96 mmol) was added to the ketone portion-wise whilst maintaining the temperature at −30° C. Upon completion of the addition, the reaction was stirred at −30° C. for 30 min and then allowed to warm to 25° C. Stirring was continued overnight and the solution was then treated with saturated ammonium chloride solution. The product was extracted into dichloromethane and this was back extracted with water and saturated brine. The dichloromethane solution was dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a crude, yellow oil (10.1 g, 100%). This compound was used directly in the next step without further purification.

후처리

  1. temperaturewhilst maintaining the temperature at −30° C
  2. additionUpon completion of the addition
  3. temperatureto warm to 25° C
  4. stirringStirring
  5. waitwas continued overnight
  6. extractionThe product was extracted into dichloromethane
  7. extractionthis was back extracted with water and saturated brine
  8. dry with materialThe dichloromethane solution was dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-066a5744eefb437fae1f1c548993669e
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233982B2

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