Phenylsilane → HCID 22259822, compound

HRID 1611071Notes

Reaction equation

HRID 1611071 reaction equation
[C:1]1([P:7]2(=O)[CH2:11][CH2:10][CH2:9][C:8]2=[CH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([SiH3])C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([P:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[CH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 12752PhenylsilaneHCID 22259816HCID 22259816, compound

Product 1

HCID 22259822HCID 22259822, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

In a 250 ml round bottom 2-neck flask charged with a magnetic stirring bar and 60 ml freshly distilled toluene, 8.5 g 1-phenyl-2-methylenephospholane-1-oxide (0.04 mol) was dissolved and 11 g of PhSiH3 was added. The flask was flushed with argon and the reaction mixture heated to 60° C. for 2 days. Then the solvent was evaporated and the residue purified by flash chromatography (hexane followed by hexane/EtOAc 15:1) to yield 7.4 g (95%) of 1-phenyl-2-methylenephospholane as a colorless oil, 1H NMR (200 MHz) δ: 1.55-2.10 (m, 4H), 2.20-2.65 (m, 2H), 5.51 (dd, 1H, J=1.6, J=11.0), 5.76 (dd, 1H, J=1.5, J=28.7), 7.05-7.50 (m, 5H), 31 P NMR (200 MHz) δ: −12.6.

Workup

  1. additionIn a 250 ml round bottom 2-neck flask charged with a magnetic stirring bar
  2. customThe flask was flushed with argon
  3. customThen the solvent was evaporated
  4. customthe residue purified by flash chromatography (hexane followed by hexane/EtOAc 15:1)

Sources & evidence

ORD record
ord-4605076a7ef24c929e05bcdc03c19178
Source dataset
uspto-grants-2006_01
Patent number
US06984744B2

Reaction notes

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