Hydrochloric Acid → Ethyl 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate

HRID 1593616ノート

反応式

HRID 1593616 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C:10]2=O)=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClC(Cl)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[S:8][C:9]3[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C:10]=3[C:4]=2[CH:3]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 69232235Ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate

生成物 1

HCID 69235740Ethyl 8-fluoro-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate収率 78.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To a room temperature solution of ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate (3.4 g, 11.5 mmol) in dichloroethane (100 mL) was added AlCl3 (3.7 g, 27.6 mmol). The mixture was heated to 80° C. for 1 hour. After cooling to room temperature, the reaction was diluted with water and acidified with 1 N HCl. The aqueous mixture was extracted with EtOAc. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated to an oil. Purification by chromatography on silica gel afforded 2.5 g (77%) of the title compound as semi-solid: MS (+) 278 (M)+.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous mixture was extracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialbrine, then was dried over MgSO4
  5. concentrationconcentrated to an oil
  6. customPurification by chromatography on silica gel

出典と根拠

ORDレコード
ord-e121c3f767dd490eb463a98701c63a91
出典データセット
uspto-grants-2007_11
特許番号
US07297704B2

反応ノート

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