Tetrahydrofuran → HCID 60206860, compound

Participants

Reaction Steps

To 0.40 mmol of hydrochloride 11 in 3 mL of acetone is added 0.29 mL (2.1 mmol) of 1-bromohexane. The mixture is heated to reflux, and 0.6 mL of a 1 M solution of potassium t-butoxide in THF (0.6 mmol) is added. After 1.2 h the mixture is cooled and aqueous 1 N KH2PO4 and ethyl acetate are added. The organic phase is washed twice with 1 N NaHCO3 and once with brine, dried over Na2SO4, and concentrated. Chromatography over silica gel, eluting with 7%-9& methanol (containing 1% of NH4OH) in CH2Cl2, affords a colorless oil. Treatment with ethereal HCl produces 147 mg (0.25 mmol, 64%) of hydrochloride 12 as a white solid: 1H NMR (CDCl3+CD3OD drop) δ 7.45 (s, 1H), 7.37 (m, 2H), 7.27 (m, 1H), 6.50 (s, 1H), 6.43 (m, 2H), 3.98 (m, 1H), 3.88 (m+t, J=6.5 Hz, 3H), 2.93 (m, 2H), 2.63 (m, 4H), 2.38 (m, 1H), 2.09 (m, 2H), 1.89 (s, 3H), 1.75 (m, 4H), 1.59 (m, 1H), 1.43-1.32 (m, 10H), 1.27 (d, J=7 Hz, 6H), 0.90 (t, J=7 Hz, 3H); MS (CI) m/z 541.5 (MH+).

Provenance & Evidence