Palmitic Acid → HCID 23039641, compound

HRID 2166426Notes

Reaction equation

HRID 2166426 reaction equation
[CH2:1]=[C:2]([CH2:5][OH:6])[CH2:3][OH:4].C1(N=C=NC2CCCCC2)CCCCC1.[C:22](O)(=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:22]([O:4][CH2:3][C:2](=[CH2:1])[CH2:5][OH:6])(=[O:38])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 3

HCID 985Palmitic AcidHCID 10868DicyclohexylcarbodiimideHCID 770481,3-Propanediol, 2-methylene-

Product 1

HCID 23039641HCID 23039641, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-Methylenepropane-1,3-diol (3.0 g) was dissolved in methylene chloride (40 ml). Dicyclohexylcarbodiimide (8.7 g), 4-dimethylaminopyridine (0.4 g) and hexadecanoic acid (8.7 g) were added. The mixture was stirred for 24 hours, filtered, and the filtrate was purified through a column of silica gel 60 (70-230 mesh, 30 g) eluting with ether/chloroform/pentane 1:1:1. The eluate was washed with saturated sodium hydrogen carbonate solution (3×70 ml), dried over anhydrous magnesium sulfate and evaporated to dryness in vacuo. 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. filtrationfiltered
  2. customthe filtrate was purified through a column of silica gel 60 (70-230 mesh, 30 g)
  3. washeluting with ether/chloroform/pentane 1:1:1
  4. washThe eluate was washed with saturated sodium hydrogen carbonate solution (3×70 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customFurther purification

Sources & evidence

ORD record
ord-a52156b5eddf4c149938cb924d04ffa3
Source dataset
uspto-grants-1990_07
Patent number
US04945098

Reaction notes

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