Acetone → 7-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

HRID 1021364

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[CH3:12][C:13](=O)[CH3:14].N1CCCC1>C1C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:10])[CH2:9][C:13]([CH3:14])([CH3:12])[O:11]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 1-(4-fluoro-2-hydroxyphenyl)ethanone (5.75 g, 37.3 mmol) and propan-2-one (12 mL, 37.3 mmol) in benzene (50 mL) was added pyrrolidine (3.11 mL, 37.3 mmol) and the reaction heated at 80° C. for 3 hours. The reaction was diluted with ethyl acetate (50 mL), washed with 1N HCl (50 mL), brine (50 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate, to provide the title compound (5.12 g, 70.7% yield).

Workup

washwashed with 1N HCl (50 mL), brine (50 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate

Sources & evidence

ORD record: ord-59f91cded47049dbb1dbcaa67bbc574a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716498B2

Linked notes

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