Triethylamine → HCID 76759590、化合物

HRID 444704ノート

反応式

HRID 444704 の反応式
[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8](=O)[CH:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].O=P(Cl)(Cl)[Cl:20].CCN(CC)CC>C(Cl)(Cl)Cl>[Cl:20][C:8]([C:3]1[S:4][CH:5]=[C:6]([CH3:7])[C:2]=1[Cl:1])=[C:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 67115664HCID 67115664、化合物

生成物 1

HCID 76759590HCID 76759590、化合物収率 66.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
5 °C

実験手順

To a solution of ethyl 3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-oxopropanoate (15.40 g, 56.67 mmol, 1 eq.) in 200 ml of CHCl3 was added POCl3 (86.9 g, 566 mmol, 10 eq.). Et3N (14.33 g, 141.6 mmol, 2.5 eq.) was added dropwise with stirring at 5° C., and the mixture was refluxed for 4 h. The mixture was evaporated. After evaporation, the mixture was diluted with DCM (CH2Cl2) and with ice water and was extracted with DCM (CH2Cl2) and washed with brine. The organic layers were combined and dried over MgSO4 before concentration under reduced pressure. The residue was subjected to column chromatography on silica gel to give ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (11 g, 66% yield) as a mixture of 2 isomers

後処理

  1. temperaturethe mixture was refluxed for 4 h
  2. customThe mixture was evaporated
  3. customAfter evaporation
  4. additionthe mixture was diluted with DCM (CH2Cl2) and with ice water
  5. extractionwas extracted with DCM (CH2Cl2)
  6. washwashed with brine
  7. dry with materialdried over MgSO4 before concentration under reduced pressure

出典と根拠

ORDレコード
ord-4847b81d5f864422aa202a73eb9b298b
出典データセット
uspto-grants-2013_07
特許番号
US08476197B2

反応ノート

読み込み中…