Lithium hexamethyldisilazane → 4-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid

(2-(4-Carboxyphenyl)ethyl)triphenylphosphonium bromide (0.58 g, 1.17 mmol) was suspended in THF (7 ml) and lithium bis(trimethylsilyl)amide was added (1M in THF, 2.46 ml). The reaction mixture turned orange and was allowed to stir for 1 hour at ambient temperature. A solution of 3-benzyloxy-2-pyridinecarbaldehyde (0.25 g, 1.17 mmol) in THF (3.5 ml) was added slowly. The reaction was stirred at ambient temperature for 1 hour. The reaction was quenched by the addition of water (8 ml) and ether (8 ml). The layers were separated, the ether layer was washed with water and the as aqueous layers were combined, acidified with 1N HCl and extracted with EtOAc (2×). The organic extracts were dried (MgSO4) and evaporated to give the title product as a mixture of isomers (2.7 g 66%).

1. stirringThe reaction was stirred at ambient temperature for 1 hour
2. customThe reaction was quenched by the addition of water (8 ml) and ether (8 ml)
3. customThe layers were separated
4. washthe ether layer was washed with water
5. extractionextracted with EtOAc (2×)
6. dry with materialThe organic extracts were dried (MgSO4)
7. customevaporated

ORD record

ord-6441c0bbfdf043f2804789475f0dcf23

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05811459