3-Nitrobenzaldehyde → HCID 67465982, compound

Temperature

-20 °C

A mixture of (methoxymethyl)triphenylphosphonium chloride (6.79 g 19.85 mmol) in anhydrous THF (50 mL) was cooled to −20° C. and potassium tert-butoxide (2.67 g. 23.82 mmol) was added in lots to give a red reaction mass. The mixture was cooled to −30° C. and a solution of 3-nitrobenzaldehyde (2.0 g, 12.12 mmol) in toluene (15 mL) was added gradually over 30 minutes. The mixture was stirred for 1 hour then EtOAc (2 mL) followed by saturated ammonium chloride were added at 0° C. The reaction mixture was extracted with EtOAc (2×75 mL). The combined organic extracts were washed with brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude compound was purified by column chromatography on neutral silica gel using DCM to afford the title compound (1.8 g, 76%) as a solid.

1. customto give a red reaction mass
2. temperatureThe mixture was cooled to −30° C.
3. additionwere added at 0° C
4. extractionThe reaction mixture was extracted with EtOAc (2×75 mL)
5. washThe combined organic extracts were washed with brine (25 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customThe crude compound was purified by column chromatography on neutral silica gel

ORD record

ord-283453f768774672b8707e34ac543ad3

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716287B2