Hydrochloric Acid → 4-(9,10-dihydro-4-oxo-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-2-yl)-4-oxobutyric acid methyl ester

HRID 2164056

반응식

HRID 2164056 반응식
[Cl-].[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([OH:9])=O.[S:11]1[CH:15]=[CH:14][C:13]2[C:16](=[O:25])[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH2:19][CH2:20][C:12]1=2.[Cl-].[Al+3].[Cl-].[Cl-].[Sn](Cl)(Cl)(Cl)Cl.Cl>C(=S)=S>[CH3:2][O:3][C:4](=[O:10])[CH2:5][CH2:6][C:7]([C:15]1[S:11][C:12]2[CH2:20][CH2:19][C:18]3[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=3[C:16](=[O:25])[C:13]=2[CH:14]=1)=[O:9]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 24287Tin tetrachlorideHCID 7684929,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-oneHCID 6451240Aluminum(III) ChlorideHCID 86605420Succinic acid methylester chloride

생성물 1

HCID 537502014-(9,10-dihydro-4-oxo-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-2-yl)-4-oxobutyric acid methyl ester

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매2회

실험 절차

A solution of 6.3 cc of succinic acid monomethyl ester chloride in 100 cc of anhydrous carbon disulphide is added dropwise at 0° to a suspension of 10.0 g of 9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one and 30.0 g of anhydrous aluminium chloride in 200 cc of anhydrous carbon disulphide, the reaction mixture is stirred for a further 6 hours at room temperature, 23.3 g of tin tetrachloride are added dropwise thereto at 20° to 25° and stirring is continued at room temperature for 15 hours. The reaction mixture is subsequently heated to 50° for 2 hours, cooled, poured on 500 cc of 5 N hydrochloric acid and extracted with chloroform. The organic phases are washed with 5 N hydrochloric acid and with water, dried over magnesium sulphate and concentrated by evaporation. The evaporation residue is dissolved in 300 cc of methylene chloride, filtered through silica gel and evaporated to dryness. The title compound crystallizes from benzene/petroleum ether and is recrystallized once from ether. M.P. 97°-98°.

후처리

  1. stirringat 20° to 25° and stirring
  2. waitis continued at room temperature for 15 hours
  3. temperatureThe reaction mixture is subsequently heated to 50° for 2 hours
  4. temperaturecooled
  5. extractionextracted with chloroform
  6. washThe organic phases are washed with 5 N hydrochloric acid and with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated by evaporation
  9. dissolutionThe evaporation residue is dissolved in 300 cc of methylene chloride
  10. filtrationfiltered through silica gel
  11. customevaporated to dryness
  12. customThe title compound crystallizes from benzene/petroleum ether
  13. customis recrystallized once from ether

출처 및 근거

ORD 기록
ord-6405bb5f8efd47b98612727ab016bef0
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04137323

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