Methacrolein → HCID 17953062, compound

HRID 1747515Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[O:13]=[CH:14][C:15](=[CH2:17])[CH3:16].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O.C1COCC1>[CH3:17][C:15](=[CH2:16])[CH:14]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:13]

Participants

Conditions

Temperature: -78 °C

Procedure

To toluene (12 mL) were added dropwise at −78° C. n-butyllithium (2.76 mol/L solution in n-hexane, 4.14 mL, 11.4 mmol) and a solution of 3-bromopyridine (1.00 mL, 10.4 mmol) in toluene (4.0 mL), and the mixture was stirred at the same temperature for 30 minutes. THF (4.0 mL) was added to the resulting suspension. After stirring at −78° C. for 15 minutes, methacrolein (1.03 mL, 12.5 mmol) was added, and the mixture was stirred for 1 hour allowing the temperature to rise slowly to room temperature. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give 2-methyl-1-(pyridin-3-yl)prop-2-en-1-ol (1.08 g, 70% yield).

Workup

stirringthe mixture was stirred for 1 hour
customto rise slowly to room temperature
extractionExtraction with ethyl acetate
washwashing with saturated brine
dry with materialdrying over anhydrous sodium sulfate
filtrationAfter filtration
customthe solvent in the filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7)

Sources & evidence

ORD record: ord-718d6fae551749efa2cfc3d7010f79c2
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150569B2

Reaction notes

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