Hexane → p-[4-(Methoxymethylene)cyclohexyl]benzonitrile

HRID 247665

반응식

HRID 247665 반응식
[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][O:10][CH3:11])C=CC=CC=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]2)=[CH:28][CH:27]=1)#[N:25].CCCCCC>COC(C)(C)C.O1CCCC1>[CH3:9][O:10][CH:11]=[C:35]1[CH2:36][CH2:37][CH:32]([C:29]2[CH:30]=[CH:31][C:26]([C:24]#[N:25])=[CH:27][CH:28]=2)[CH2:33][CH2:34]1

참가 물질

6

반응물 3

HCID 8058HexaneHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 157899134-(4-Oxocyclohexyl)benzonitrile

생성물 1

HCID 19739357p-[4-(Methoxymethylene)cyclohexyl]benzonitrile수율 94%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
-10 °C

실험 절차

10.4 g of triphenyl-methoxymethyl-phosphonium chloride were suspended in 60 ml of t-butyl methyl ether while gassing with argon in a sulphonation flask equipped with a thermometer, a mechanical stirrer, a dropping funnel and a solid substance addition tube and the suspension was treated with 3.6 g of solid potassium t-butylate at -10° C. within 10 minutes. After completion of the addition the mixture was stirred for a further 30 minutes at -10° C. then the deep orange, heterogeneous reaction mixture was treated dropwise at 0° C. with a solution of 4.2 g of 4-(p-cyanophenyl)cyclohexanone in 50 ml of absolute tetrahydrofuran. The reaction mixture was subsequently stirred for a futher 2 hours at room temperature, then poured into 500 ml of hexane and filtered. Low-pressure chromatography (0.5 bar) of the concentrated residue (7.1 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95) gave 4.5 g (94%) of p-[4-(methoxymethylene)cyclohexyl]benzonitrile as a colourless oil; purity 95%, Rf-value (ethyl acetate/petroleum ether vol. 1:9) 0.30.

후처리

  1. customwhile gassing with argon in a sulphonation flask
  2. customequipped with a thermometer, a mechanical stirrer, a dropping funnel and a solid substance addition tube
  3. additionAfter completion of the addition the mixture
  4. stirringThe reaction mixture was subsequently stirred for a futher 2 hours at room temperature
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-d6c674e663f746899d345b4bb69ffe77
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04709030

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