Lithium Hydroxide → 5-(3-Chlorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylic acid

HRID 1036994ノート

反応式

HRID 1036994 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([O:15]CC)=[O:14])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 58066749Ethyl 5-(3-chlorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylate

生成物 1

HCID 580667535-(3-Chlorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylic acid

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

182 mg (0.50 mmol) of the compound from Example 17A are provided in 2 ml of dioxane, and 4.4 ml (8.80 mmol) of a 2N aqueous lithium hydroxide solution are added. The mixture is stirred at 50° C. for 2 hours and subsequently concentrated. The residue is diluted with water, a concentrated aqueous HCl solution is added until an acidic pH is obtained and the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 159 mg (95% of theory) of the title compound are obtained.

後処理

  1. concentrationsubsequently concentrated
  2. additionThe residue is diluted with water
  3. additiona concentrated aqueous HCl solution is added until an acidic pH
  4. customis obtained
  5. extractionthe mixture is extracted with dichloromethane
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

出典と根拠

ORDレコード
ord-b2ecb932acf143009bc64aad17843aea
出典データセット
uspto-grants-2013_10
特許番号
US08546438B2

反応ノート

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