Ethanol → HCID 15926974, compound

HRID 478096Notes

Reaction equation

HRID 478096 reaction equation
[Cl-:1].[OH:2][CH:3]([CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N+:11]([CH3:14])([CH3:13])[CH3:12].C(O)C.[CH2:38]=[C:39]1[O:43][C:41](=[O:42])[CH2:40]1>N1C=CC=CC=1>[Cl-:1].[C:41]([O:2][CH:3]([CH2:15][O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][N+:11]([CH3:12])([CH3:13])[CH3:14])(=[O:42])[CH2:40][C:39]([CH3:38])=[O:43]

Participants

5

Reactant 3

HCID 702EthanolHCID 12661DiketeneHCID 15058551HCID 15058551, compound

Product 1

HCID 15926974HCID 15926974, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
45 °C

Procedure

1.5 g (2.94 millimole) of 2-[2-[2-hydroxy-3-(octadecyloxy)propyloxy]ethoxy]ethyltrimethylammonium chloride was dissolved in 80 ml of pyridine, to which 2 ml of diketene was added, and the mixture was stirred at 45° C. for 5 minutes. 10 ml of ethanol was added thereto, and the mixture was concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (Merck Co., Art.7734, 38 g, Eluant; chloroform-methanol=4:1-2:1), to give 1.5 g (86%) of the above-captioned compound.

Workup

  1. additionwas added
  2. concentrationthe mixture was concentrated to dryness under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (Merck Co., Art.7734, 38 g, Eluant; chloroform-methanol=4:1-2:1)

Sources & evidence

ORD record
ord-4651ebd9cfba418d8816b296e8b8cc13
Source dataset
uspto-grants-1989_12
Patent number
US04889953

Reaction notes

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