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

HRID 2384865ノート

反応式

HRID 2384865 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-5a9183086b4b4ae987c3acfffa42056a
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

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