Methanol → 2-Cyano-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}-acrylic acid

HRID 987233ノート

反応式

HRID 987233 の反応式
C([O:3][C:4](=[O:29])[C:5]([C:27]#[N:28])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)C.[OH-].[Li+].CO>O>[C:27]([C:5](=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[C:4]([OH:29])=[O:3])#[N:28].[C:27]([C:5](=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[C:4]([OH:29])=[O:3])#[N:28]

参加物

6

反応物 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 865950572-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}acrylic acid ethyl ester

生成物 2

HCID 696292652-Cyano-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}-acrylic acidHCID 865950582-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]-phenyl}acrylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

2-Cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}acrylic acid ethyl ester (described in Example 6) (0.201 g; 0.483 mmole), lithium hydroxide (0.04 g; 1.67 mmole), methanol (2.3 ml) and water (2.3 ml) was stirred at 40° C. for 23 hours. More water was added, methanol was removed by evaporation in vacuo and the mixture was acidified using potassium hydrogen sulfate. The mixture was extracted with ethyl acetate and the organic phase was dried (sodium sulfate), filtered and evaporated in vacuo. The crude products were purified on preparative HPLC using acetonitrile (gradient 30-60%): ammonium acetate (0.1 M). The fractions were acidified with potassium hydrogen sulfate and then extracted with ethyl acetate. The organic phases were combined and evaporated in vacuo to give 7 mg of 2-cyano-3-{4-[2-(4-methanesulfonyloxyphenyl)ethoxy]-phenyl}acrylic acid and 21,8 mg of 2-cyano-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}-acrylic acid.

後処理

  1. custommethanol was removed by evaporation in vacuo
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude products were purified on preparative HPLC
  7. extractionextracted with ethyl acetate
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-0b325fc0d41f45b39f6d5adff9c37d64
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

反応ノート

読み込み中…