O-Cresol → HCID 57871398, compound

Participants

Reaction Steps

Cool a CH2CL2 (20 mL) solution of 7-(1-ethyl-1-hydroxypropyl)naphthalene-2-carboxylic acid methyl ester (0.73 g, 2.68 mmol) and o-cresol (1.54 mL, 15.0 mmol) to −78° C.; then dropwise add BF3-OEt2 (0.76 mL, 6.0 mmol). Allow the reaction mixture to warm to RT and stir for 1 h. Quench the reaction with ice water. Dilute the resulting mixture with EtOAc (200 mL). Wash the mixture with brine, dry the organic layer over Na2SO4, filter and concentrate the filtrate. Purify by silica gel radial chromatography (5:95 to 35:65 EtOAc:hex) to give the title compound as a yellow oil (0.93 g, 86%). MS (ES) m/e 363 (M+1).

Provenance & Evidence