Potassium Phosphate, Tribasic → 2-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

HRID 509156Notes

Reaction equation

Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 2-bromo-3-methoxy-cyclopent-2-enone (6.75 g, 35.3 mmol), 2,4,6-trimethylphenyl boronic acid (6.99 g, 42.6 mmol) and freshly ground potassium phosphate (15 g, 70.6 mmol) in degassed toluene (180 ml) under nitrogen are added Pd(OAc)2 (159 mg, 0.71 mmol) and S-Phos (579 mg, 1.41 mmol), and the reaction heated to 90° C. with stirring under N2 for 4 hours. The reaction mixture is partitioned between ethyl acetate (150 ml) and water (150 ml), and the organic layer is removed, Silica gel is added to the organic layer, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 2-(2,4,6-trimethylphenyl)-3-methoxy-cyclopent-2-enone (6.2 g).

Workup

customThe reaction mixture is partitioned between ethyl acetate (150 ml) and water (150 ml)
customthe organic layer is removed
additionSilica gel is added to the organic layer
customthe solvent is evaporated under reduced pressure
customthe residue is purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-322cfeffc88d47a0b5314d424c032dea
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096560B2

Reaction notes

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