ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Potassium Cyanide → trans-3-(beta-Cyanostyryl)-2,2-dimethyl-cyclopropanecarboxylic acid, alpha-cyano-m-(p-chlorophenoxy)benzyl ester

HRID 443985
ノート
印刷プレビュー

反応式

HRID 443985 の反応式
S(Cl)(Cl)=O.[C:5]([C:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:8][CH:9]1[CH:11]([C:12]([OH:14])=[O:13])[C:10]1([CH3:16])[CH3:15])#[N:6].[Cl:23][C:24]1[CH:38]=[CH:37][C:27]([O:28][C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[CH:32]=O)=[CH:26][CH:25]=1.C1OCCOCCOCCOCCOCCOC1.[C-:57]#[N:58].[K+]>C1(C)C=CC=CC=1.O>[C:57]([CH:32]([O:13][C:12]([C@H:11]1[C@H:9]([CH:8]=[C:7]([C:5]#[N:6])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:10]1([CH3:16])[CH3:15])=[O:14])[C:31]1[CH:34]=[CH:35][CH:36]=[C:29]([O:28][C:27]2[CH:37]=[CH:38][C:24]([Cl:23])=[CH:25][CH:26]=2)[CH:30]=1)#[N:58]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 9032Potassium CyanideHCID 24386Thionyl ChlorideHCID 2855718-Crown-6HCID 6160153-(4-Chlorophenoxy)benzaldehydeHCID 571159863-(beta-Cyanostyryl)-2,2-dimethyl-cyclopropanecarboxylic acid

生成物 1

HCID 86737699trans-3-(beta-Cyanostyryl)-2,2-dimethyl-cyclopropanecarboxylic acid, alpha-cyano-m-(p-chlorophenoxy)benzyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

Thionyl chloride (1.61 ml, 2.6 g; 0.022 mole), 3-(β-cyanostyryl)-2,2-dimethyl-cyclopropanecarboxylic acid (4.82 g; 0.02 mole) and toluene are mixed and heated at 100° C. for 1 hour. The reaction mixture is cooled to 25° C. and a solution of m-(p-chlorophenoxy)benzaldehyde (4.65 g; 0.02 mole) and 18-crown-6 (0.49 g; 0.002 mole) in toluene (10 ml) is added. To this reaction mixture a solution of potassium cyanide (2.6 g; 0.04 mole) in water (6 ml) is added slowly while maintaining the temperature between 20°-25° C. The reaction mixture is then stirred for 18 hours at room temperature. The resultant black reaction mixture is poured in water and extracted with ether (3X). The combined ether extracts are washed with water, 10% hydrochloric acid, 10% sodium bicarbonate, water and saturated sodium chloride solution. The ether layer is dried over sodium sulfate and evaporated in vacuo to leave a brown gum. This gum is purified by dry column chromatography (silica gel; eluent: 1:1 methylene chloride:hexane) to afford the title product, a yellow glass (1.0 g, 8.6%).

後処理

  1. temperatureThe reaction mixture is cooled to 25° C.
  2. temperaturewhile maintaining the temperature between 20°-25° C
  3. customThe resultant black reaction mixture
  4. extractionextracted with ether (3X)
  5. washThe combined ether extracts are washed with water, 10% hydrochloric acid, 10% sodium bicarbonate, water and saturated sodium chloride solution
  6. dry with materialThe ether layer is dried over sodium sulfate
  7. customevaporated in vacuo
  8. customto leave a brown gum
  9. customThis gum is purified
  10. dry with materialby dry column chromatography (silica gel; eluent: 1:1 methylene chloride:hexane)

出典と根拠

ORDレコード
ord-cb8830cb168642a199f4f08b09617df9
出典データセット
uspto-grants-1981_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04262117

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート