Nicotinic Acid → HCID 69927467, compound

HRID 849981Notes

Reaction equation

HRID 849981 reaction equation
C1(N=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12]C2)CCCCC1.C(O)(=[O:23])C1C=CC=NC=1.[CH2:25]([O:43][CH2:44][CH2:45][CH2:46][OH:47])[CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C(Cl)Cl>[C:25]([O:43][CH2:44][CH2:45][CH2:46][O:47][CH2:12][C:13]1[CH:14]=[CH:15][CH:10]=[N:9][CH:8]=1)(=[O:23])[CH2:26][CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32]/[CH:33]=[CH:34]\[CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 86755077HCID 86755077, compound

Product 1

HCID 69927467HCID 69927467, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,3-Dicyclohexylcarbodiimide (211 g, 1.02 mol) and 4-(N,N-dimethylaminopyridine (141 g, 1.15 mol) in methylene chloride (2000 ml) were added with stirring to a solution of nicotinic acid (131 g, 1.07 mol) and 1-(z,z,z-octadeca-6,9,12-trienyloxy)-3-hydroxypropane (300 g, 0.89 mol) in methylene chloride (2000 ml). The progress of reaction was monitored by tlc. On completion, the reaction mixture was filtered and the organic layer washed with 2M hydrochloric acid (2000 ml) and water (3×2000 ml), dried with magnesium sulphate and concentrated under reduced pressure. Purification by dry column chromatography using a gradient of ethyl acetate in hexane yielded 1-(z,z,z-octadeca-6,9,12-trienoyloxy)-3-(nicotinyloxy)-propane as a pale yellow oil in 81% yield.

Workup

  1. customThe progress of reaction
  2. filtrationOn completion, the reaction mixture was filtered
  3. washthe organic layer washed with 2M hydrochloric acid (2000 ml) and water (3×2000 ml)
  4. dry with materialdried with magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. customby dry column chromatography

Sources & evidence

ORD record
ord-dd522dc1588b463d97962281ecbd9a7e
Source dataset
uspto-grants-2000_01
Patent number
US06015821

Reaction notes

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