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

HRID 874018

Reaction equation

HRID 874018 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

HCID 580672642,2,6,6-Tetramethyl-1-(2',4',6'-triisopropylbiphenyl-2-yl)phosphinan-4-oneYield 76.1%

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-40464b5c60ca44498c0e57962ad1be83
Source dataset
uspto-grants-2015_03
Patent number
US08975443B2

Linked notes

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