Trifluoroacetic acid → HCID 20131150, compound

HRID 845484Notes

Reaction equation

HRID 845484 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:12]O2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(=[S:32])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:12][S:32]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 19758Phosphine sulfide, triphenyl-HCID 1085579586088-36-0

Product 1

HCID 20131150HCID 20131150, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-(3-phenylpropyl)oxirane (Example 35b) (2.0 g, 0.0123 mol) and triphenylphosphine sulphide (3.62 g, 0.0123 mol) in toluene (20 ml), trifluoroacetic acid (1.40 g, 0.0123 mol) was added over 5 min. After stirring for 1 hour at room temperature, the reaction mixture was washed with water, sodium hydrogen carbonate solution and again with water. After drying (MgSO4) and removal of solvent at reduced pressure, the product contaminated with triphenylphosphine oxide was isolated as a crystalline mass. Attempted purification of the thiirane resulted in its extensive decomposition and it was therefore used in its crude state.

Workup

  1. washthe reaction mixture was washed with water, sodium hydrogen carbonate solution and again with water
  2. customAfter drying
  3. custom(MgSO4) and removal of solvent at reduced pressure
  4. customwas isolated as a crystalline mass
  5. customAttempted purification of the thiirane
  6. customresulted in its extensive decomposition and it

Sources & evidence

ORD record
ord-44564354df9c44daa7a2d2e90bd28914
Source dataset
uspto-grants-1988_07
Patent number
US04758573

Reaction notes

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