Water → 5,6-Dihydro-4-oxo-5-(2-ethoxycarbonylethyl)thieno[2,3-b]thiopyran

HRID 2254310ノート

反応式

HRID 2254310 の反応式
S(Cl)(Cl)=O.[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[S:10][CH2:11][CH:12]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([OH:15])=O.Cl[Sn](Cl)(Cl)Cl.O>CN(C=O)C.C(Cl)Cl>[O:15]=[C:13]1[CH:12]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][S:10][C:6]2[S:5][CH:9]=[CH:8][C:7]1=2

参加物

7

反応物 4

HCID 962WaterHCID 24287Tin tetrachlorideHCID 24386Thionyl ChlorideHCID 19745039HCID 19745039、化合物

生成物 1

HCID 678831665,6-Dihydro-4-oxo-5-(2-ethoxycarbonylethyl)thieno[2,3-b]thiopyran収率 97.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

Under N2, thionyl chloride (5.5 g, 0.043 mol) was added dropwise to a solution of 1 (11.5 g, 0.04 mol) in DMF (4 drops) and methylene chloride (100 ml). After the addition, the solution was stirred at room temperature for 4.5 hours. The mixture was then cooled to -10° and SnCl4 (5.3 g, 0.02 mol) was added dropwise. After the addition the reaction was allowed to stir at room temperature for 28 hours. The mixture was then added to H2O and the aqueous layer extracted with EtOAc (3×). The organic extracts were backwashed with saturated NaHCO3, dried, filtered and concentrated to dryness to yield 10.5 g (97%) of 2 wherein R1, R2, R3 and R4 are each H.

後処理

  1. additionAfter the addition
  2. temperatureThe mixture was then cooled to -10°
  3. additionAfter the addition the reaction
  4. stirringto stir at room temperature for 28 hours
  5. extractionthe aqueous layer extracted with EtOAc (3×)
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-bd2fb372f93746fea05d5cdb04a35fba
出典データセット
uspto-grants-1993_08
特許番号
US05235059

反応ノート

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