2,4-Dihydroxybenzaldehyde → HCID 58934503, compound

HRID 855029Notes

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8](O)[CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:11][C:12]([F:22])([F:21])[CH2:13]/C=C/C(OCC)=O.C(=O)([O-])[O-:24].[K+].[K+].[C:29]([O:32][CH2:33][CH3:34])(=[O:31])[CH3:30]>>[OH:24][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH:13]([C:12]([F:22])([F:21])[F:11])[C:30]([C:29]([O:32][CH2:33][CH3:34])=[O:31])=[CH:4]2

Participants

Reactant 4

HCID 72132,4-Dihydroxybenzaldehyde

HCID 8857Ethyl Acetate

HCID 11430Potassium Carbonate

HCID 15104041Ethyl 5,5,5-trifluoropent-2-enoate

Product 1

HCID 58934503HCID 58934503, compoundYield 98%

Conditions

Temperature: 90 °C

Procedure

A mixture of 10 g (72.5 mmol) of 2,4-dihydroxybenzaldehyde, 15.3 mL (101.4 mmol) of ethyl 4-triflouromethylcrotonate, and 20 g (145 mmol) of potassium carbonate in 25 mL of anhydrous dimethylformmamide was heated to 90° C. for three h. After cooling to room temperature, the reaction was added to 500 mL of ethyl acetate. The organic phase was washed with brine three times, dried over anhydrous magnesium sulfate and concd in vacuo. Silica chromatography with EtOAc/hexane (3:7) gave 19.0 g (98%) of a yellow solid: 1H NMR (CDCl3/400 MHz) 7.63 (s, 1H), 6.85(d, J=8.8 Hz, 1H), 6.79(dd, J=8.8 Hz, 2.8 Hz, 1H), 6.70(d, J=2.8 Hz, 1H), 5.63(q, J=6.8 Hz, 1H), 4.31(m, 2H), 1.34(t, J=7.2 Hz, 3H). MS (ESI+) 289.1 (M+1, 100).

Workup

temperatureAfter cooling to room temperature
washThe organic phase was washed with brine three times
dry with materialdried over anhydrous magnesium sulfate and concd in vacuo

Sources & evidence

ORD record: ord-f7654d4c5b4b4a7f8c061b9a5b789063
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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