Nitrogen → Dicyclohexyl(2,4,6-trimethoxyphenyl)phosphine

反応式

[CH3:1][O:2][C:3]1[C:4](OC)=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.N#N.Cl[P:21]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1C[O:37][CH2:36]C1>>[CH:22]1([P:21]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:4]2[C:5]([O:9][CH3:10])=[CH:6][C:7]([O:37][CH3:36])=[CH:8][C:3]=2[O:2][CH3:1])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

参加物

反応物 5

HCID 947Nitrogen

HCID 8028Tetrahydrofuran

HCID 124621,2,3-Trimethoxybenzene

HCID 2734135Chlorodicyclohexylphosphine

HCID 178418339Butyllithium

生成物 1

HCID 46867875Dicyclohexyl(2,4,6-trimethoxyphenyl)phosphine収率 25%

実験手順

To a solution of trimethoxybenzene (1.0062 g, 6 mmol) in 20 mL of dry THF was added n-butyl lithium (2.6 mL, 2.5 M in hexane, 6.6 mmol) dropwise under N2. The mixture was stirred for 4.5 hours at room temperature, at which time the reaction system was then cooled to −78° C. Chlorodicyclohexyl phosphine was added dropwise. After the mixture is stirred for 30 minutes, the reaction system was warmed up to room temperature and stirred for another 18 hours. Extraction with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and purified by column chromatography (petroleum ether/ethyl acetate=10/1˜5/1) afforded 0.5514 g of product. The yield is 25%.