Pyridine → 2-Tridecyloxyethyl 2-trimethylammonioethyl phosphate

HRID 1719793Notes

Reaction equation

HRID 1719793 reaction equation
[CH2:1]([O:14][CH2:15][CH2:16][OH:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[P:18](Cl)(Cl)(=[O:23])[O:19]CCBr.[N:26]1[CH:31]=CC=C[CH:27]=1.[CH:32](Cl)(Cl)Cl.[CH3:36][C:37](C)=[O:38]>C1C=CC=CC=1>[P:18]([O-:19])([O:38][CH2:37][CH2:36][N+:26]([CH3:31])([CH3:32])[CH3:27])([O:17][CH2:16][CH2:15][O:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 38049Tridecyl ethyleneglycol monoetherHCID 4684632(2-Bromoethoxy)phosphonoyl dichlorideHCID 15930782Chloroform acetone

Product 1

HCID 131166522-Tridecyloxyethyl 2-trimethylammonioethyl phosphateYield 34%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In benzene were dissolved 3.8 g of 2-n-tridecyloxyethanol and 5.7 g of 2-bromoethyl phosphorodichloridate, and following dropwise addition of 1.85 g of pyridine under ice-cooling, the mixture was stirred at room temperature. The reaction mixture was treated by the procedure of Production Example 1 including hydrolysis, quaternization, dehalogenation, purification by silica gel column chromatography and recrystallization from chloroform-acetone to give 2.2 g (34%) of the desired product. It was hygroscopic.

Workup

  1. temperaturecooling

Sources & evidence

ORD record
ord-26ab19b79ca04b3c8dde86b7c39abe02
Source dataset
uspto-grants-1985_09
Patent number
US04542219

Reaction notes

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