Phorone → 2,2,6,6-Tetramethyl-1-(2',4',6'-triisopropylbiphenyl-2-yl)phosphinan-4-one

HRID 78967

Reaktionsgleichung

Reaktionsgleichung von HRID 78967
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[PH2:22])([CH3:3])[CH3:2].[CH3:23][C:24](=[CH:26][C:27](=[O:32])[CH:28]=[C:29]([CH3:31])[CH3:30])[CH3:25]>>[CH3:30][C:29]1([CH3:31])[CH2:28][C:27](=[O:32])[CH2:26][C:24]([CH3:25])([CH3:23])[P:22]1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:5]1[C:6]([CH:13]([CH3:14])[CH3:15])=[CH:7][C:8]([CH:10]([CH3:11])[CH3:12])=[CH:9][C:4]=1[CH:1]([CH3:2])[CH3:3]

Komponenten

3

Edukt 2

HCID 10438PhoroneHCID 58067324(2',4',6'-Triisopropylbiphenyl-2-yl)phosphine

Produkt 1

HCID 580672642,2,6,6-Tetramethyl-1-(2',4',6'-triisopropylbiphenyl-2-yl)phosphinan-4-oneAusbeute 76,1 %

Versuchsvorschrift

A flask was charged with 10.8 g of (2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (66% potent, 7.13 g, 22.8 mmol, 1.0 equiv) and 6.6 g of 2,6-dimethyl-2,5-heptadien-4-one (47.7 mmol, 2.1 equiv). The vessel was purged with argon gas and immersed in an oil bath at 170° C. with magnetic stirring. The flask was sealed with a Teflon stopcock and the reaction was allowed to proceed under a static argon atmosphere. The flask was removed from the oil bath after 14 h and the contents allowed to cool to room temperature under argon gas. Anhydrous ethanol (70 mL) was added to the unpurified solids and the solids were broken up manually. The slurry was warmed to 80° C., held for an hour, and cooled to room temperature. The product was isolated by filtration, washes with ethanol and dried in vacuo to give 7.82 g of 2,2,6,6-tetramethyl-1-(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphinan-4-one (98 area % by HPLC, 74% yield).

Aufarbeitung

  1. customThe vessel was purged with argon gas
  2. customimmersed in an oil bath at 170° C. with magnetic stirring
  3. customThe flask was sealed with a Teflon stopcock
  4. customThe flask was removed from the oil bath after 14 h
  5. additionAnhydrous ethanol (70 mL) was added to the unpurified solids
  6. temperatureThe slurry was warmed to 80° C.
  7. waitheld for an hour
  8. temperaturecooled to room temperature
  9. customThe product was isolated by filtration, washes with ethanol
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-54673f2980d9402bb4a9a95815311f66
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841487B2

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