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

HRID 1470788Notes

Reaction equation

[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

Participants

Reactant 5

HCID 947Nitrogen

HCID 8028Tetrahydrofuran

HCID 124621,2,3-Trimethoxybenzene

HCID 2734135Chlorodicyclohexylphosphine

HCID 178418339Butyllithium

Product 1

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

Procedure

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%.

Workup

temperaturewas then cooled to −78° C
stirringAfter the mixture is stirred for 30 minutes
temperaturethe reaction system was warmed up to room temperature
stirringstirred for another 18 hours
extractionExtraction with ethyl acetate
washwashed with water
dry with materialdried over anhydrous sodium sulfate
custompurified by column chromatography (petroleum ether/ethyl acetate=10/1˜5/1)

Sources & evidence

ORD record: ord-c206c13ed9aa433d937ca5e5dfff0158
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006491B2

Reaction notes

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