Nicotinic Acid → HCID 9929262, compound

HRID 849980Notes

Reaction equation

HRID 849980 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([OH:24])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.[CH2:25](O)[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]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:16]([O:24][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]/[CH:37]=[CH:36]\[CH2:35]/[CH:34]=[CH:33]\[CH2:32]/[CH:31]=[CH:30]\[CH2:29][CH2:28][CH2:27][CH2:26][CH3:25])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1

Participants

6

Reactant 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 9795274gamma-Linolenyl alcohol

Product 1

HCID 9929262HCID 9929262, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

1,3-Dicyclohexylcarbodiimide (97 g, 0.49 mol) and 4-(N,N-dimethylamino)pyridine (65 g, 0.53 mol) in methylene chloride (800 ml) were added with stirring to a solution of nicotinic acid (60 g, 0.49 mol) and z,z,z-octadeca-6,9,12-trienol (107 g, 0.41 mol) in methylene chloride (1200 ml). The progress of the reaction was monitored by tlc. On completion, the reaction mixture was filtered and the organic layer washed with 2M hydrochloric acid (500 ml) and water (3×500 ml), dried with magnesium sulphate and concentrated under reduced pressure. Purification by dry column chromatography using a gradient of ethyl acetate in hexane yielded z,z,z-octadeca-6,9,12-trienyl nicotinate as a pale yellow oil in 91% yield.

Workup

  1. filtrationOn completion, the reaction mixture was filtered
  2. washthe organic layer washed with 2M hydrochloric acid (500 ml) and water (3×500 ml)
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customPurification
  6. customby dry column chromatography

Sources & evidence

ORD record
ord-2903e275a5864633b91ab20894073ba8
Source dataset
uspto-grants-2000_01
Patent number
US06015821

Reaction notes

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