3-Chloro-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzaldehyde → 2-Chloro-4-ethenylphenol

Temperature

0 °C

To a slurry of methyltriphenylphosphonium bromide (0.23 g) in dry THF (5 ml) under nitrogen at −78° C., n-butyl lithium (1.6M in hexanes, 0.37 ml) was added dropwise over 2 min. The mixture was allowed to warm to 0° C., stirred for 20 min, cooled to −78° C. and a solution of 3-chloro-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzaldehyde* (0.134 g) in dry THF (5 ml) added. The reaction mixture was allowed to reach room temperature overnight and quenched with saturated aqueous ammonium chloride. The resultant mixture was extracted with diethyl ether and the combined organic extracts were concentrated under reduced pressure. The residue was purified using SPE (silica, eluting with cyclohexane, followed by 5% to 25% ethyl acetate:cyclohexane) to give the title compound (0.049 g) as an oil. *Boukouvalas, J; Maltais, F; Lachance, N., Tetrahedron Lett. (1994), 35(43), 7897–900.

1. temperaturecooled to −78° C.
2. waitto reach room temperature overnight
3. customquenched with saturated aqueous ammonium chloride
4. extractionThe resultant mixture was extracted with diethyl ether
5. concentrationthe combined organic extracts were concentrated under reduced pressure
6. customThe residue was purified
7. washSPE (silica, eluting with cyclohexane, followed by 5% to 25% ethyl acetate:cyclohexane)

ORD record

ord-ae0f49a59f394151a37927a4235f4ff1

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084139B2