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

HRID 443985

반응식

HRID 443985 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 1140Toluene용매2회

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-cb8830cb168642a199f4f08b09617df9
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04262117

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