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

HRID 26988

Reaktionsgleichung

Reaktionsgleichung von HRID 26988
[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]

Komponenten

5

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1c0b5f3210f745a995389c63ca02bf59
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04151357

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