Tetrahydrofuran → Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate

HRID 918148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 918148
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].C1COCC1.[CH3:18][C:19]([CH3:29])([CH2:25][CH2:26][CH2:27][CH3:28])[C:20](OCC)=[O:21]>C(O)(=O)C>[O:21]=[C:20]([C:19]([CH3:29])([CH3:18])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 12958Dimethyl methylphosphonateHCID 3024116Ethyl dimethylhexanoateHCID 178418339Butyllithium

Produkt 1

HCID 13018035Dimethyl (3,3-dimethyl-2-oxoheptyl)phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

n-Butyllithium (400 ml.) is added slowly to a solution of dimethyl methylphosphonate (73.7 g.) in 1.3 l. of THF at about -66° C. To the mixture is added a solution of ethyl 2,2-dimethylhexanoate (53 g.) in 150 ml. of THF, and the resulting mixture is stirred at -70° C. for 2 hrs. Then, 46 ml. of acetic acid is added, and the mixture is concentrated under reduced pressure. The residue is mixed with portions of dichloromethane (about 1.2 l.) and water (about 150 ml.), shaken, and separated. The organic phase is dried over magnesium sulfate and concentrated. Distillation yields the title compound, 41.6 g., b.p. 117°-120° C./1 mm.

Aufarbeitung

  1. customat about -66° C
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionThe residue is mixed with portions of dichloromethane (about 1.2 l.) and water (about 150 ml.)
  4. customseparated
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationDistillation

Quellen und Nachweise

ORD-Eintrag
ord-9e331fbc28c7452185a2a0b9e4653ace
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03969396

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