p-Toluenesulfonic acid monohydrate → 2-(4-Chloro-phenyl)-4,5-dihydro-thieno[2,3-c]pyran-7-one

HRID 2384865노트

반응식

HRID 2384865 반응식
C[O:2][C:3]([C:5]1[S:6][C:7]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:8][C:9]=1[CH2:10][CH2:11][OH:12])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:7]2[S:6][C:5]3[C:3](=[O:2])[O:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)=[CH:14][CH:15]=1

참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 689499765-(4-Chloro-phenyl)-3-(2-hydroxy-ethyl)-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 689489532-(4-Chloro-phenyl)-4,5-dihydro-thieno[2,3-c]pyran-7-one수율 43%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Dissolve 5-(4-chloro-phenyl)-3-(2-hydroxy-ethyl)-thiophene-2-carboxylic acid methyl ester (3.4 g, 11.46 mmol) in toluene (60 mL) and add p-toluenesulfonic acid monohydrate (0.3 g, 1.58 mmol) and heat to 80° C. for one hour. Cool the mixture to room temperature and dilute with ethyl acetate (50 mL). Wash the solution with 1 N NaOH and extract the aqueous portion twice with ethyl acetate. Combine the organic fractions, dry over Na2SO4, filter, and concentrate. Triturate the solid with ether and then filter and dry under vacuum to give 1.3 g (43%) of the title compound. LC-MS/ES m/z (35Cl) 265.0 [M+H]+.

후처리

  1. temperatureCool the mixture to room temperature
  2. washWash the solution with 1 N NaOH
  3. extractionextract the aqueous portion twice with ethyl acetate
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customTriturate the solid with ether
  8. filtrationfilter
  9. customdry under vacuum

출처 및 근거

ORD 기록
ord-5a9183086b4b4ae987c3acfffa42056a
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

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