Pyridine → HCID 23039610, compound

HRID 2166428Notes

Reaction equation

HRID 2166428 reaction equation
[CH2:1]=[C:2]([CH2:5][OH:6])[CH2:3][OH:4].[CH2:7]([O:23][C:24](Cl)=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].N1C=CC=CC=1>C(Cl)Cl>[CH2:7]([O:23][C:24]([O:4][CH2:3][C:2](=[CH2:1])[CH2:5][OH:6])=[O:25])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 770481,3-Propanediol, 2-methylene-HCID 97633Cetyl chloroformate

Product 1

HCID 23039610HCID 23039610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

2-Methylenepropane-1,3-diol (5.0 g), hexadecyloxycarbonylchloride (17.4 g) and pyridine (4.4 g) was dissolved in methylene chloride (60 ml). The mixture was stirred for 2.5 hours at 22° C. The mixture was purified through a column of silica gel 60 (70-230 mesh, 30 g), eluting with ether/chloroform 1:1. Further purification was achieved by chromatography on a Waters PrepLC®-System 500A using a PrepPAK®-500-SILICA cartridge with ether/chloroform/pentane 1:1:3 as eluent.

Workup

  1. customThe mixture was purified through a column of silica gel 60 (70-230 mesh, 30 g)
  2. washeluting with ether/chloroform 1:1
  3. customFurther purification

Sources & evidence

ORD record
ord-fbf0b50dfed64e1b9b3368cc30c81277
Source dataset
uspto-grants-1990_07
Patent number
US04945098

Reaction notes

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