Toluene → 2-(4-Vinylphenyl)pyridine

HRID 1265318Notes

Reaction equation

[H-].[Na+].[C:3]1(C)C=CC=CC=1.[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[CH:14][CH:13]=1)=[CH2:3]

Participants

Conditions

Temperature: 110 °C

Procedure

Methyltriphenylphophonium bromide (25 g, 0.07 mol), sodium hydride (NaH, 3.36 g, 0.14 mol), and toluene (100 ml) were placed into 250 ml of 2-necked round-bottomed flask under N2. The reaction mixture was refluxed at 110° C. for 3 hr while changing the reaction solution to orange color. After cooling the reaction mixture, 2-(4-formyl-phenyl)pyridine (10 g, 0.0545 mol) was added and further refluxed at 110° C. for 12 hr. The reaction mixture was poured in 300 ml of water in beaker and extracted then with ether (3×150 ml). The ether layer was then dried over magnesium sulfate (10 g) by stirring for 30 min. The dried ether layer was evaporated in vacuo to dryness and purified further by column chromatography on silica gel with eluting hexane/ethylacetate (1/10) to yield 2-(4-vinyl-phenyl)pyridine (85%).

Workup

additionwas added
temperaturefurther refluxed at 110° C. for 12 hr
extractionextracted
dry with materialThe ether layer was then dried over magnesium sulfate (10 g)
customThe dried ether layer was evaporated in vacuo to dryness
custompurified further by column chromatography on silica gel with eluting hexane/ethylacetate (1/10)

Sources & evidence

ORD record: ord-dd249ded33134447a9c65d3b1f6f6320
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545159B2

Reaction notes

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