Benzaldehyde → HCID 68109410, compound

Participants

Reaction Steps

A solution of the product of Example 29 step B (1.0 g, 2.58 mmol) in dry THF (15 mL) was cooled to −78° C. under a nitrogen atmosphere and n-butyl lithium (1.6 M in hexane, 1.0 mL, 1.54 mmol) was added dropwise over 10 min. The reaction mixture was stirred for 20 min and a solution of benzaldehyde (137 mg, 1.29 mmol) in THF (1 mL) was added over 5 min. The reaction was stirred for 1 h at −78° C., poured into saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was dried over Na2SO4, concentrated in vacuo and the residue purified by flash column chromatography (SiO2, 85:15 hexanes/ethyl acetate) to afford tert-butyl 6-chloro-8-(hydroxy(phenyl)methyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (0.6 g, 56%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.42-7.26 (m, 7H), 5.91 (d, J=3.3 Hz, 1H), 4.51 (s, 2H), 3.87-3.75 (m, 2H), 2.93-2.83 (m, 2H), 2.28 (d, J=3.3 Hz, 1H), 1.49 (s, 9H).

Provenance & Evidence