Triphenylphosphine → 3-Methyl-4-(5-fluorobenzofur-7-yl)pentan-2-one

HRID 1824971Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](Br)[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[CH3:12][C:13]([CH:15]([OH:17])[CH3:16])=[CH2:14].[C:18]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>CN(C)P(N(C)C)(N(C)C)=O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][CH:13]([CH:12]([C:4]1[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=[C:2]([F:1])[CH:3]=1)[CH3:18])[C:15](=[O:17])[CH3:16]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1 gm (4.65 mMol) 5-fluoro-7-bromobenzofuran, 0.54 ml (5.23 mMol) 2-methyl-3-hydroxybut-1-ene, 9 mg (0.04 mMol) palladium(II) acetate, 0.021 gm (0.08 mMol) triphenylphosphine, and 0.44 gm (5.23 mMol) sodium bicarbonate in 5 mL hexamethylphosphoramide was heated at 130° C. for 3.5 hours. The reaction mixture was cooled to room temperature and was then diluted with 100 mL diethyl ether. The organic phase was washed sequentially with 2×20 mL water followed by 2×20 mL saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 10:1 hexane:diethyl ether. Fractions containing the desired product were combined and concentrated under reduced pressure to provide the desired product in 81% yield as a colorless oil.

Workup

temperatureThe reaction mixture was cooled to room temperature
washThe organic phase was washed sequentially with 2×20 mL water
dry with materialThe remaining organics were dried over sodium sulfate
concentrationconcentrated under reduced pressure
washeluting with 10:1 hexane
additionFractions containing the desired product
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-25e0a10bc84240c287ebd700c260e67d
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045545B1

Reaction notes

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