2,4,6-Trimethylpyridine → HCID 15153821, compound

HRID 578609Notes

Reaction equation

HRID 578609 reaction equation
N1C(C)=CC(C)=CC=1C.[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].[C:22](Cl)(=[O:26])[C:23]([CH3:25])=[CH2:24]>ClCCl>[Br:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:26])[C:23]([CH3:25])=[CH2:24]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 13528Methacryloyl chlorideHCID 1045071-Decanol, 10-bromo-

Product 1

HCID 15153821HCID 15153821, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2,4,6-Collidin (12.3 ml, 92.7 mmol, 1.1 eq.) was added to a solution of 10-bromodecanol (20.0 g, 84.3 mmol) in anhydrous dichloromethane (200 ml). After cooling the mixture to 0° C. methacrylic acid chloride (16.5 ml, 168.6 mmol, 2 eq.) was slowly added dropwise and the reaction mixture was stirred for 1 h at 0° C. and at for 15 h room temperature. The reaction mixture was then washed with water (100 ml) and cold 1N HCl (100 ml). The combined organic phases were dried with anhydrous sodium sulphate. After removal of the solvent under reduced pressure the obtained crude product was purified by column chromatography (eluent: hexane/dichloromethane 8:2). 18.0 g (70% yield) of the product was obtained as a colorless liquid.

Workup

  1. additionwas slowly added dropwise
  2. washThe reaction mixture was then washed with water (100 ml) and cold 1N HCl (100 ml)
  3. dry with materialThe combined organic phases were dried with anhydrous sodium sulphate
  4. customAfter removal of the solvent under reduced pressure the
  5. customobtained crude product
  6. customwas purified by column chromatography (eluent: hexane/dichloromethane 8:2)

Sources & evidence

ORD record
ord-115dfc1246384b20bdc0e7770cb99700
Source dataset
uspto-grants-2015_05
Patent number
US09040602B2

Reaction notes

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