Triethylamine → (E,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol diisonicotinate

HRID 2049990

Reaction equation

HRID 2049990 reaction equation
[OH:1][CH2:2]/[C:3](/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:4]/[CH2:5][CH2:6]/[C:7](/[CH3:11])=[CH:8]/[CH2:9][OH:10].C(N(CC)CC)C.Cl.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1>C(Cl)(Cl)Cl>[C:31]([OH:38])(=[O:1])[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1.[C:31]([OH:38])(=[O:1])[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1.[OH:1][CH2:2]/[C:3](/[CH2:12][CH2:13]/[CH:14]=[C:15](\[CH3:22])/[CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:4]/[CH2:5][CH2:6]/[C:7](/[CH3:11])=[CH:8]/[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6373042(2E,6E)-2-[(3E)-4,8-Dimethylnona-3,7-dien-1-YL]-6-methylocta-2,6-diene-1,8-diolHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 86736498(E,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol diisonicotinate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.0 g of (E,Z,E) and (E,E,E)-7-hydroxymethyl-3,11,15-trimethyl-2,6,10,14-hexadecatetraen-1-ol in 30 ml of anhydrous chloroform was added 3.0 ml of triethylamine and then 2.0 g of isonicotinoyl chloride hydrochloride dropwise at room temperature. Stirring was continued for 3 hours. The reaction mixture was poured into ice-water, extracted with chloroform, washed with aqueous sodium hydrogencarbonate and water and dried over anhydrous sodium sulfate. The solvent was distilled off to give an oily substance, which was then purified by a column chromatography with silica gel (20 g) to afford 1.4 g of the end product.

Workup

  1. customdropwise at room temperature
  2. extractionextracted with chloroform
  3. washwashed with aqueous sodium hydrogencarbonate and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto give an oily substance, which
  7. customwas then purified by a column chromatography with silica gel (20 g)

Sources & evidence

ORD record
ord-4e0c91aa093346c096ecbb3e29e29f2f
Source dataset
uspto-grants-1980_04
Patent number
US04199519

Linked notes

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