Triethylamine → 4-[(Diphenoxyphosphinyl)oxy]-2,5-dihydro-3-thiophenecarboxylic acid methyl ester

HRID 128706

Reaktionsgleichung

Reaktionsgleichung von HRID 128706
[C:1]([CH:5]1[C:9](=[O:10])[CH2:8][S:7][CH2:6]1)([O:3][CH3:4])=[O:2].C(N(CC)CC)C.[C:18]1([O:24][P:25](Cl)([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH3:4][O:3][C:1]([C:5]1[CH2:6][S:7][CH2:8][C:9]=1[O:10][P:25]([O:24][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([O:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:26])=[O:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 75654Diphenyl chlorophosphateHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester

Produkt 1

HCID 536975314-[(Diphenoxyphosphinyl)oxy]-2,5-dihydro-3-thiophenecarboxylic acid methyl esterAusbeute 108,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-carbomethoxytetrahydrothiophene-4-one (Gianturco M. A., Friedel P., Giammarino A. S., Tetrahedron, 20:1772 (1964)) (4.0 g, 25 mmol) and triethylamine (6.6 g, 65 mmol) in 50 mL dry THF at 0° was added, over a 15 minute period, diphenylchlorophosphate (17.5 g, 65 mmol). The reaction mixture was stirred at room temperature for 2 days, then treated with ice-cold water and extracted with diethyl ether. The extracts were washed with saturated NaHCO3, brine, dried with Na2SO4, and evaporated to yield an oil (10.6 g).

Aufarbeitung

  1. additiontreated with ice-cold water
  2. extractionextracted with diethyl ether
  3. washThe extracts were washed with saturated NaHCO3, brine
  4. dry with materialdried with Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-561e0249275f4c94b431010641f51009
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464855

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