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Hydrochloric Acid → Diethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl2-naphthyl)-1-ethenyl]-benzenephosphonate

HRID 2073602
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2073602
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([P:16]([O:21][CH2:22][CH3:23])(=[O:20])[O:17][CH2:18][CH3:19])=[CH:12][CH:11]=1)(OCC)=O)C.[H-].[Na+].[CH:26]([C:28]1[CH:37]=[CH:36][C:35]2[C:34]([CH3:39])([CH3:38])[CH2:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]=2[CH:29]=1)=O.Cl>CS(C)=O>[CH3:38][C:34]1([CH3:39])[CH2:33][CH2:32][C:31]([CH3:41])([CH3:40])[C:30]2[CH:29]=[C:28](/[CH:26]=[CH:9]/[C:10]3[CH:11]=[CH:12][C:13]([P:16]([O:17][CH2:18][CH3:19])(=[O:20])[O:21][CH2:22][CH3:23])=[CH:14][CH:15]=3)[CH:37]=[CH:36][C:35]1=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 104208875,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehydeHCID 19857614Diethyl 4diethylphosphonomethylbenzenephosphonate

Produkt 1

HCID 14371701Diethyl (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl2-naphthyl)-1-ethenyl]-benzenephosphonateAusbeute 32,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel3×

Versuchsvorschrift

A solution of 22 g (53 millimoles) of diethyl 4diethylphosphonomethylbenzenephosphonate in 100 ml of dimethyl sulfoxide was added dropwise to a suspension of 1.8 g (64 millimoles) of sodium hydride in 50 ml of dry dimethyl sulfoxide at room temperature. Stirring was continued for 1 hour, after which a solution of 8.7 g (40 millimoles) of 2-formyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene in 75 ml of dimethyl sulfoxide was added dropwise. Stirring was continued for 16 hours at room temperature and the mixture was poured onto water, acidified with 2N hydrochloric acid and extracted three times with ether. The combined organic phases were washed twice with water and twice with saturated sodium chloride solution, dried over sodium sulfate and evaporated down. The residue was purified by column chromatography (silica gel; heptane/0.55 - 10% ethyl acetate) to give 5.5 g of the title compound of melting point 83°-84° C.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 16 hours at room temperature
  3. additionthe mixture was poured onto water
  4. extractionextracted three times with ether
  5. washThe combined organic phases were washed twice with water and twice with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated down
  8. customThe residue was purified by column chromatography (silica gel; heptane/0.55 - 10% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-98588f0719b248a09e5a0e3597845832
Quelldatensatz
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04918212

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