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Acetic Acid → Dimethyl (3-methyl-2-oxooct-5-yn-1-yl)phosphonate

HRID 1902666
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1902666
C([Li])CCC.[CH3:6][O:7][P:8]([CH3:12])(=[O:11])[O:9][CH3:10].[CH3:13][CH:14]([CH2:16][C:17]#[C:18][CH2:19][CH3:20])[CH3:15].C(O)(=[O:23])C>CCCCCC.O1CCCC1>[CH3:6][O:7][P:8]([CH2:12][C:13](=[O:23])[CH:14]([CH3:15])[CH2:16][C:17]#[C:18][CH2:19][CH3:20])(=[O:11])[O:9][CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 1431226-Methyl-3-heptyneHCID 178418339Butyllithium

Produkt 1

HCID 13269867Dimethyl (3-methyl-2-oxooct-5-yn-1-yl)phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028Tetrahydrofuran
Lösungsmittel
2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

646 ml of a 1.52% butyl lithium solution in hexane is dripped into a solution of 176 g of methane phosphonic acid dimethylester in 2 liters of tetra-hydrofuran at -70° C.; the mixture is stirred for 15 minutes and slowly a solution of 82.5 g of 2-methyl-hept-4-yne acid ethylester in 320 ml of tetrahydrofuran is added. This mixture is stirred for 4 h at -70° C., neutralized with acetic acid and vacuum evaporated. The residue is reacted with 200 ml of water, extracted three times with 600 ml of methylene chloride each time, the organic extract is shaken once with 100 ml of water, dried over magnesium sulfate and vacuum evaporated. The distillation of the residue in a 0.6 torr vacuum and at 120° C. yields 85 g of the title compound in the form of a colorless liquid.

Aufarbeitung

  1. stirringThis mixture is stirred for 4 h at -70° C.
  2. customevaporated
  3. customThe residue is reacted with 200 ml of water
  4. extractionextracted three times with 600 ml of methylene chloride each time
  5. extractionthe organic extract
  6. stirringis shaken once with 100 ml of water
  7. dry with materialdried over magnesium sulfate and vacuum
  8. customevaporated
  9. distillationThe distillation of the residue in a 0.6 torr vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fd8719da1d9e48beb35c4592ad10d64b
Quelldatensatz
uspto-grants-1982_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04364950

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