Phosphinic Acid → HCID 86759308, Verbindung

HRID 432974

Reaktionsgleichung

Reaktionsgleichung von HRID 432974
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].[C:31](O)(=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48].[PH2](O)=O>>[C:31]([O:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:30])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=[O:49])[CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38]/[CH:39]=[CH:40]\[CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Komponenten

4

Edukt 3

HCID 4124402Phosphinic AcidHCID 5280933Gamma-Linolenic acidHCID 59118692HCID 59118692, Verbindung

Produkt 1

HCID 86759308HCID 86759308, Verbindung

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 1-hydroxy-3-(z-15-tetracosenoyloxy)propane, prepared according to Description 3, (0.045 mol, 19.0 g), z,z,z-6,9,12-octadecatrienoic acid (0.054 mol, 15.0 g) and hypophosphorous acid (0.4 g) was heated with stirring to 160° C. under nitrogen. After 5 h, TLC (80:18:2 petroleum ether-ethyl ether-acetic acid) indicated that most of the mono-ester had reacted (Rf: 0.60). The mixture was cooled down to room temperature and petroleum ether (800 mL) was added. The resulting solution was washed with saturated sodium bicarbonate (3×80 mL) and saturated sodium chloride (3×80 mL). It was then dried over anhydrous sodium sulphate, concentrated and purified by flash chromatography on silica gel (19:1 petroleum ether-ethyl ether) to yield 1-(z,z,z-6,9,12-octadecatrienoyloxy)-3-(z-15-tetracosenoyloxy)propane as a pale yellow oil.

Aufarbeitung

  1. customprepared
  2. temperaturewas heated
  3. customhad reacted (Rf: 0.60)
  4. temperatureThe mixture was cooled down to room temperature
  5. washThe resulting solution was washed with saturated sodium bicarbonate (3×80 mL) and saturated sodium chloride (3×80 mL)
  6. dry with materialIt was then dried over anhydrous sodium sulphate
  7. concentrationconcentrated
  8. custompurified by flash chromatography on silica gel (19:1 petroleum ether-ethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-509117f4412d48a78b57464e78a9390b
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664406B1

Verknüpfte Notizen

Wird geladen…