4-(1H-imidazol-1-yl)benzaldehyde → (E)-4-[4-(1H-Imidazol-1-yl)phenyl]-3-butenoic acid

HRID 974992

反応式

HRID 974992 の反応式
[N:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl-].[C:15]([CH2:18][CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:17])=[O:16].CC(C)([O-])C.[K+]>O1CCCC1>[N:1]1([C:6]2[CH:13]=[CH:12][C:9](/[CH:10]=[CH:19]/[CH2:18][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

参加物

5

反応物 3

HCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 10270534(2-Carboxyethyl)triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 15045263(E)-4-[4-(1H-Imidazol-1-yl)phenyl]-3-butenoic acid収率 75.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-50 °C

実験手順

5.45 g of 4-(1H-imidazol-1-yl)benzaldehyde and 12.93 g of β-carboxyethyltriphenylphosphonium chloride were suspended in 70 ml of tetrahydrofuran. The obtained suspension was cooled to -50° C. and vigorously stirred. 30 ml of a solution of 7.83 g of potassium t-butoxide in tetrahydrofuran was gradually added dropwise to the resulting suspension. The temperature of the obtained mixture was gradually raised to 0° C. After one hour, ice-water was added to the mixture. The obtained mixture was washed with ether. The pH of the aqueous layer was adjusted with concentrated hydrochloric acid to about 4 to precipitate a solid. This solid was recovered by filtration and washed with water and methanol to obtain 5.44 g of the title compound as a pale yellow powder (yield: 75%).

後処理

  1. temperatureThe temperature of the obtained mixture was gradually raised to 0° C
  2. washThe obtained mixture was washed with ether
  3. customto precipitate a solid
  4. filtrationThis solid was recovered by filtration
  5. washwashed with water and methanol

出典と根拠

ORDレコード
ord-46081e00b0b449a8a676a45098cc2ce3
出典データセット
uspto-grants-1997_03
特許番号
US05607953

関連ノート

読み込み中…