Trifluoroacetic acid → 2-(1,1,1-trifluoro-2-methylpropan-2-yl)-4H-pyran-4-one

HRID 1050157Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]([CH3:14])([CH3:13])/[C:4](/O)=[CH:5]/[C:6](=[O:11])/[CH:7]=[CH:8]/[O:9]C.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[F:16][C:2]([F:1])([F:15])[C:3]([C:4]1[O:9][CH:8]=[CH:7][C:6](=[O:11])[CH:5]=1)([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of (1E,4Z)-7,7,7-trifluoro-5-hydroxy-1-methoxy-6,6-dimethylhepta-1,4-dien-3-one (1 g, 4.20 mmol) in toluene (5 mL) was added TFA (0.647 mL, 8.40 mmol). The mixture was stirred at 25° C. for 16 h. Then the mixture was concentrated to afford 2-(1,1,1-trifluoro-2-methylpropan-2-yl)-4H-pyran-4-one (800 mg, 3.10 mmol, 73.9% yield). TLC (PE/EA=1:1, Rf=0.2): 1H NMR (400 MHz, CD3OD): δ 8.12 (d, J=6.0 Hz, 1H), 6.53 (d, J=2.4 Hz, 1H), 6.39 (dd, J=2.4, 6.0 Hz, 1H), 1.53 (s, 6H). ES-LCMS m/z 207.1 (M+H).

Workup

concentrationThen the mixture was concentrated

Sources & evidence

ORD record: ord-af6c9b324f9d42d2996a904f5b683d7c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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