Water → HCID 86642124, compound

Temperature

-10 °C

To a suspension of (methoxymethyl)triphenylphosphonium chloride (7.37 g, 21.5 mmol) in THF (100 mL) at −10° C. was added LDA (1.8M in THF/hexane/ethylbenzene, 11.94 mL, 21.5 mmol). The resulting red suspension was stirred at −10° C. for 1 h. To this was added a solution of 6-bromopyridine-2-carboxaldehyde (2.0 g, 10.8 mmol) in THF (60 mL). The resulting colourless suspension was slowly warmed to r.t. over 2.5 h. The reaction mixture was poured into water and extracted with Et2O (3×75 mL). The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo to give a pale yellow oil. Purification by column chromatography (SiO2, 20:1 heptane:EtOAc) gave the title compound (506 mg, 22%) as a yellow oil. δH (CDCl3) 7.61 (1H, d, J 12.6 Hz), 7.37 (1H, t, J 7.7 Hz), 7.16 (1H, dd, J 7.9 and 0.8 Hz), 6.98 (1H, dd, J 7.5 and 0.6 Hz), 5.78 (1H, d, J 12.6 Hz), 3.73 (3H, s). LCMS (ES+) 215.97 (M+H)+, RT 3.50 minutes (Method 1).

1. temperatureThe resulting colourless suspension was slowly warmed to r.t. over 2.5 h
2. extractionextracted with Et2O (3×75 mL)
3. washThe combined organic phases were washed with brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customto give a pale yellow oil
7. customPurification by column chromatography (SiO2, 20:1 heptane:EtOAc)

ORD record

ord-a53759a3928442a28626675b4abdd60f

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242116B2