Diethyl Ether → 1,1-Diphenylacetone

HRID 864492

Reaktionsgleichung

Reaktionsgleichung von HRID 864492
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]([Sn](CCCC)(CCCC)COCC1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)CCC.C(OCC)C.[F-].[K+]>C(Cl)(Cl)Cl>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](=[O:9])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 746372,2-Diphenylacetyl chlorideHCID 522689Potassium FluorideHCID 85682165Tri-n-butyl-((3,5-bis(trifluoromethyl)phenyl)methyloxymethyl)tin

Produkt 1

HCID 699071,1-Diphenylacetone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Diphenylacetyl chloride (4.6 g), tri-n-butyl-((3,5-bis(trifluoromethyl)phenyl)methyloxymethyl)tin (12.6 g; Example 1a, (Method Ai)and benzylchlorobis(triphenylphosphine) palladium (II)(80 mg)were dissolved in chloroform (10 ml) and the solution heated at 80° C. for 6h. On cooling diethyl ether and saturated aqueous potassium fluoride were added and after 30 minutes the solution was filtered through Hiflo™. The organic layer was washed with water, saturated brine and dried (MgSO4). After evaporation in vacuo the residual oil was purified by chromatography on silica gel (eluting with 0 to 10% ethyl acetate in petroleum ether bp=60°-80° C.) to give 1-(3,5-bis(trifluoromethyl)phenyl)methyloxy)-3,3-diphenyl acetone as an oil. 1H NMR (CDCl3, 360MHz) δ7.80 (1H; s; 4-aryl CH) 7.71 (2H; s; 2,6-aryl CH), 7.43-7.24 (10H; m; phenyl), 5.30 (1H; s; Ph2CH), 4.56 (2H; s), 4.31 (2H; s). m/e Found 452.1191, C24H13F6O2 requires 452.12110.

Aufarbeitung

  1. additionwere added and after 30 minutes the solution
  2. filtrationwas filtered through Hiflo™
  3. washThe organic layer was washed with water, saturated brine
  4. dry with materialdried (MgSO4)
  5. customAfter evaporation in vacuo the residual oil
  6. customwas purified by chromatography on silica gel (eluting with 0 to 10% ethyl acetate in petroleum ether bp=60°-80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-cfa0d90d320c4607a1d2e6bcdc8c5fd8
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05563161

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