Water → 2-Oxo-5-phenoxypentylidenetriphenylphosphorane

HRID 1389181

Reaktionsgleichung

Reaktionsgleichung von HRID 1389181
C([Li])CCC.[O:6]=[C:7]([CH3:28])[CH:8]=[P:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O:29]([CH2:36][CH2:37]Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>CCCCCC.O1CCCC1.[2H]C(Cl)(Cl)Cl.C(OCC)C>[O:6]=[C:7]([CH2:28][CH2:37][CH2:36][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:8]=[P:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 68526Benzene, (2-bromoethoxy)-HCID 178418339Butyllithium

Produkt 1

HCID 202985512-Oxo-5-phenoxypentylidenetriphenylphosphoraneAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 71583Chloroform-DLösungsmittel

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

A solution of n-butyl lithium (2.69 g) in hexane (26.25 ml) was added dropwise to a stirred solution of 2-oxopropylidenetriphenylphosphorane (12.73 g) in anhydrous tetrahydrofuran (400 ml) at -65° C. in an atmosphere of dry nitrogen. The red solution was stirred at -65° C. for a further 15 minutes and was then treated with a solution of 2-phenoxyethyl bromide (8.04 g) in anhydrous tetrahydrofuran (40 ml). The mixture was stirred at 0° C. for one hour and then at ambient temperature for 2 hours, and was poured into water and extracted with diethyl ether. The organic solution was washed with water then dried over magnesium sulphate. Evaporation of the solution gave a yellow gum which slowly hardened on prolonged storage after trituration with diethyl ether to give crude 2-oxo-5-phenoxypentylidenetriphenylphosphorane (8.0 g), m.p. 83°-89° C. [elemental analysis: P, 7.4%; C29H27O2P requires P, 7.1%. νmax 715, 755, 1110, 1400, 1445, 1490 and 1555 cm-1. NMR (approximately 10% w/v solution in deuterochloroform): multiplets at 6.7-7.9δ and 1.8-2.7δ, triplet at 4.0δ (J=6 cycles/second)].

Aufarbeitung

  1. stirringThe mixture was stirred at 0° C. for one hour
  2. waitat ambient temperature for 2 hours
  3. extractionextracted with diethyl ether
  4. washThe organic solution was washed with water
  5. dry with materialthen dried over magnesium sulphate
  6. customEvaporation of the solution
  7. customgave a yellow gum which

Quellen und Nachweise

ORD-Eintrag
ord-e6fe9ce61f554ec7a6551492dbfe4684
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04243683

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