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

HRID 1778614Notes

Reaction equation

HRID 1778614 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-603a78be32a940babf79e9c54820a6a1
Source dataset
uspto-grants-2016_02
Patent number
US09266913B2

Reaction notes

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