反応式
[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]1参加物
反応条件
- 温度
- -10 °C
実験手順
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.
後処理
- customwhile gassing with argon in a sulphonation flask
- customequipped with a thermometer, a mechanical stirrer, a dropping funnel and a solid substance addition tube
- additionAfter completion of the addition the mixture
- stirringThe reaction mixture was subsequently stirred for a futher 2 hours at room temperature
- filtrationfiltered
出典と根拠
- ORDレコード
- ord-d6c674e663f746899d345b4bb69ffe77
- 出典データセット
- uspto-grants-1987_11
- 特許番号
- US04709030
関連ノート
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