Hydrochloric Acid → (+/-)-5-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid

HRID 660982ノート

反応式

HRID 660982 の反応式
C([O:3][C:4]([C:6]1[S:7][C:8]([CH:11]([O:13][C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[C:16]([CH3:31])[CH:15]=2)[CH3:12])=[CH:9][CH:10]=1)=[O:5])C.[OH-].[Li+].Cl>C1COCC1>[CH3:20][C:18]1[CH:19]=[C:14]([O:13][CH:11]([C:8]2[S:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][CH:9]=2)[CH3:12])[CH:15]=[C:16]([CH3:31])[C:17]=1[C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67485105(+/-)-5-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester

生成物 1

HCID 67485022(+/-)-5-[1-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid収率 92.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a mixture of (±)-5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester (0.636 g, 1.42 mmol) in THF (14 mL) is added lithium hydroxide (1N aqueous, 14 mL). The mixture is warmed to 70° C. and stirred overnight. The reaction mixture is acidified with 1N HCl (15 mL), extracted into ethyl acetate (3×25 mL), dried over MgSO4, and concentrated, to provide (±)-5-[1-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid (0.552 g, 92%) as a white foam. MS (ES): 419.2 [M−H]−.

後処理

  1. extractionextracted into ethyl acetate (3×25 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-2bb39986a0aa43d6838c330d4b6ea79f
出典データセット
uspto-grants-2011_12
特許番号
US08084489B2

反応ノート

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