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

HRID 1036994노트

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HRID 1036994 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b2ecb932acf143009bc64aad17843aea
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546438B2

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