Sodium Chloride → Ethyl (2E)-3-phenyl-2-butenoate

HRID 16647

反応式

HRID 16647 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[C:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)[CH3:18].[Cl-].[Na+]>O1CCCC1>[C:20]1(/[C:17](/[CH3:18])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 7410AcetophenoneHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

生成物 1

HCID 5354836Ethyl (2E)-3-phenyl-2-butenoate収率 128.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
50 °C

実験手順

A mixture of 10 g (0.25 mol) of sodium hydride and tetrahydrofuran is heated to 50° C., followed by dropwise addition over 30 minutes of a solution of 48 ml (0.19 mol) of ethyl diethylphosphonoacetate in 80 ml of tetrahydrofuran. A solution of 28.4 g (0.24 mol) of acetophenone in 60 ml of tetrahydrofuran is added dropwise at 0° C. and the mixture is stirred for 16 hours at 25° C. 250 ml of saturated sodium chloride solution are added at 0° C. and the resulting mixture is extracted with ether. The organic phase is dried (Na2SO4) and the solvents are evaporated off under reduced pressure. The 46.6 g of product obtained are purified by flash chromatography (90/10 cyclohexane/diisopropyl ether) (29 g; 63%).

後処理

  1. extractionthe resulting mixture is extracted with ether
  2. dry with materialThe organic phase is dried (Na2SO4)
  3. customthe solvents are evaporated off under reduced pressure

出典と根拠

ORDレコード
ord-e57508df4c494718b30ab937cbf2203a
出典データセット
uspto-grants-2010_06
特許番号
US07737176B2

関連ノート

読み込み中…