Pyridine → Methyl 4-bromo-3-oxooctadecanoate

HRID 1384497Notes

Reaction equation

HRID 1384497 reaction equation
C[C:2]1(C)[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])O1.N1C=CC=CC=1.[Br:17][CH:18]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])C(Cl)=O>ClCCCl>[Br:17][CH:18]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:4](=[O:5])[CH2:6][C:7]([O:9][CH3:2])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 111319562-Bromohexadecanoyl chloride

Product 1

HCID 21187102Methyl 4-bromo-3-oxooctadecanoate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1.8 mol of Meldrum's acid were mixed with 3.96 mol of pyridine in a round-bottomed flask containing 1,2-dichloroethane, placed at 0° C. under argon and with stirring. 1.98 mol of 2-bromohexadecanoyl chloride were then introduced slowly and the mixture was left stirring for 2 hours at 0° C.

Workup

  1. customplaced at 0° C. under argon
  2. waitthe mixture was left
  3. stirringstirring for 2 hours at 0° C.

Sources & evidence

ORD record
ord-b0f50c532c124e609ad86ec4c8489a05
Source dataset
uspto-grants-2001_07
Patent number
US06258977B1

Reaction notes

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