4-Toluenesulfonyl chloride → HCID 22734543, compound

Participants

Reaction Steps

(7,8-Dihydro-6H-5-oxa-1-aza-phenanthren-6-yl)-methanol (0.27 g, 1.3 mmole) was dissolved in 75 mL of methylene chloride and p-toluenesulfonyl chloride (0.60 g, 3.1 mmole) added. The mixture was placed in an ice/isopropanol bath and first N,N-diisopropylethylamine (0.55 mL, 3.1 mmole) and then N,N-dimethyaminopyridine added. The mixture was allowed to stir under nitrogen for 5 days. It was washed with 150 mL portions of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuum to an orange oil. Column chromatography on silica gel with 0–5% methanol/methylene chloride gave 0.22 g of the title compound. 1H-NMR (CDCl3): doublet 8.8 δ (1 H); doublet 8.25 δ (1 H); doublet 7.8 δ (2 H); doublet 7.6 δ (1 H); multiplet 7.3 δ (4 H); multiplet 4.4 δ (1 H); doublet 4.3 δ (2 H); multiplet 2.9 δ (2 H); singlet 2.4 δ (3 H); multiplet 2.0 δ (2 H).

Provenance & Evidence