Water → HCID 86668198, compound

HRID 243807Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2([CH3:17])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][C:4]=1[CH:5]=[O:6].F[B-](F)(F)F.[O:23]=[N+:24]=[O:25].O>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:10]([N+:24]([O-:25])=[O:23])=[CH:9][C:8]([C:11]2([CH3:17])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

Conditions

Temperature: -40 °C

Procedure

A solution of the crude product containing 2-methoxy-5-(4-methyltetrahydro-2H-pyran-4-yl)benzaldehyde (0.719 g) in ethyl acetate (10.0 mL) was cooled to −40° C., and nitronium tetrafluoroborate (0.597 g, 4.49 mmol) was added thereto. The resulting mixture was stirred for 2 hours while raising the temperature to −10° C. Water was added to the reaction solution and the resulting solution was diluted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure, and the obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=90/10-30/70) to obtain 0.644 g of the captioned compound (92% yield in 2 steps).

Workup

temperaturewhile raising the temperature to −10° C
washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe solvent was then evaporated under reduced pressure
customthe obtained residue was purified by column chromatography (silica gel, hexane/ethyl acetate=90/10-30/70)

Sources & evidence

ORD record: ord-206fd1ff2f9e48c9b58bf15c99656995
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653304B2

Reaction notes

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