Triethylamine → (2-Bromoethyl)phosphonochloridic acid

HRID 235699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235699
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Br:7][CH2:8][CH2:9][P:10](=[O:13])([OH:12])[OH:11].[CH2:14]([O:21][CH:22]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:23][OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C(O)C.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Br:7][CH2:8][CH2:9][P:10]([Cl:2])(=[O:13])[OH:11].[CH2:27]([O:26][CH2:25][CH:22]([O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:23][O:24][P:10]([CH2:9][CH2:8][Br:7])(=[O:11])[O-:12])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 3613627(2-Bromoethyl)phosphonic AcidHCID 131165252-(Benzyloxy)-3-(octadecyloxy)propan-1-OL

Produkt 2

HCID 53742859(2-Bromoethyl)phosphonochloridic acidHCID 86741267Mono[3-(octadecyloxy)-2-(benzyloxy)propyl](2-bromoethyl)phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

(2-Bromoethyl)phosphonic acid monochloride was prepared from phosphorous pentachloride and (2-bromoethyl)phosphonic acid according to E. Baer and N. Z. Stanacey, J. BIOL. CHEM., 10: 3754 (1965). A portion of this reagent was dissolved in about 50 ml of anhydrous, ethanol-free chloroform, cooled in an ice-water bath to about 10° C. To this was added a portion of 2-(benzyloxy)-3-(octadecyloxy)-1-propanol and about 3.0 ml of dry triethylamine in about 50 ml of dry chloroform, under argon, with stirring over a period of one hour. The reaction was allowed to stand at room temperature about 48 hours, then was refrigerated at about 0° C. overnight and then taken to dryness. The residue was dissolved in toluene, filtered and the filtrate taken to dryness. The residue was extracted with ether, giving the desired title compound as a pale yellow syrup.

Aufarbeitung

  1. waitto stand at room temperature about 48 hours
  2. waitwas refrigerated at about 0° C. overnight
  3. filtrationfiltered
  4. extractionThe residue was extracted with ether

Quellen und Nachweise

ORD-Eintrag
ord-c4b9ec15d7b845b1a5b6298575ec4a95
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

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