Triphenylphosphine → HCID 45090107, compound

HRID 1245407Notes

Reaction equation

HRID 1245407 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1OS(C(F)(F)F)(=O)=O)=[O:4].[CH2:18]([Sn](CCCC)(CCCC)C=C)[CH2:19]CC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[CH:18]=[CH2:19])=[O:4]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 10880291methyl 2-(((trifluoromethyl)sulfonyl)oxy)cyclopent-1-enecarboxylate

Product 1

HCID 45090107HCID 45090107, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Palladium (II) acetate (0.095 g) was added to a solution of the product from step 27a (1.62 g, 5.9 mmol), tributyl(vinyl)tin (1.72 mL, 5.9 mmol), and triphenylphosphine (0.215 g, 0.82 mmol) in THF (20 mL) under a nitrogen atmosphere. The reaction was heated to 50° C. for 3 h, cooled to room temperature and concentrated. The residue was purified by FCC on silica gel eluting ethyl ether:hexanes (2:98) to give 2-vinyl-cyclopent-1-enecarboxylic acid methyl ester (0.53 g, 59%) as an oil.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by FCC on silica gel
  4. washeluting ethyl ether:hexanes (2:98)

Sources & evidence

ORD record
ord-df2bafb072f64ac49602958ab42b4e5c
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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