Pivalaldehyde → HCID 67276267, compound

Temperature

-78 °C

To a stirred solution of 1-bromo-4-(propylthio)benzene (500 mg, 2.16 mmol) in THF (10 ml) at −78° C. was added n-butyllithium (2.5 M in hexanes, 0.91 ml, 2.27 mmol). The resulting yellow solution was stirred at −78° C. for 15 minutes then pivaldehyde (0.29 ml, 2.59 mmol) was added. The mixture was allowed to warm to room temperature, during which time the solution turned colourless. The mixture was partitioned between ethyl acetate (60 ml) and water (30 ml). The organic phase was separated, washed with brine (30 ml), dried over MgSO4 filtered and evaporated to give a colourless oil. The crude product was chromatographed on silica eluting with 5% ethyl acetate in hexanes to give the title product as a pale yellow oil (468 mg). 1H NMR δ (CDCl3) 7.28-7.20 (4H, m), 4.36 (1H, s), 2.89 (2H, t, J=7.3 Hz), 1.84 (1H, s), 1.71-1.63 (2H, m), 1.02 (3H, t, J=7.3 Hz), 0.91 (9H, s).

1. temperatureto warm to room temperature, during which time the solution
2. customThe mixture was partitioned between ethyl acetate (60 ml) and water (30 ml)
3. customThe organic phase was separated
4. washwashed with brine (30 ml)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customto give a colourless oil
9. customThe crude product was chromatographed on silica eluting with 5% ethyl acetate in hexanes

ORD record

ord-331db6f73fe54a1d9363bf74134a5d5f

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163956B2