4-Toluenesulfonyl chloride → HCID 15870294, compound

Participants

Reaction Conditions

Reaction Steps

A solution of p-toluenesulfonyl chloride (17.01 g, 89.2 mmol) in CH2 Cl2 (300 mL) was added to a solution of II (8.89 g, 47.0 mmol) in 1N NaOH (300 mL) which had been cooled to 0° C. After addition was complete, the biphasic mixture was stirred for 14 hours (0° C. to room temperature). The layers were separated and the aqueous portion was extracted with CH2Cl2 (2×50 mL). The combined organic phase was washed with 1N HCl (2×100 mL) and (100 mL) and evaporated in vacuo. Column chromatography on silica gel eluting with 3% EtOH/CHCl3 produced 7.46 g (39%) of III. NMR δ 0.77 (d, 3 H, J=7), 1.15 (t, 3 H, J=7), 1.45-1.76 (m, 2 H), 2.40 (s, 6 H), 2.79-3.25 (m, 4 H), 3.70-4.08 (m, 1 H), 5.47 (t, 1 H, J=7), 7.13-7.81 (m, 8 H).

Provenance & Evidence