Ammonium Chloride → HCID 86218651、化合物

HRID 590508

反応式

HRID 590508 の反応式
[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]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 178461836HCID 178461836、化合物

生成物 1

HCID 86218651HCID 86218651、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-066a5744eefb437fae1f1c548993669e
出典データセット
uspto-grants-2016_01
特許番号
US09233982B2

関連ノート

読み込み中…