Dimethylformamide → HCID 22292431, compound

Participants

Reaction Steps

POCl3 (3.4 mL, 0.036 mol) was added dropwise to a solution of 61 (4.9 g, 0.023 mol) and dry DMF (3.5 mL, 0.045 mol) in 1,2-dichloroethane (100 mL) at 0° C. The resultant mixture was refluxed for 2 hours, poured into ice water and neutralized by addition of 6 M sodium carbonate. The reaction mixture was extracted with methylene chloride (3×100 mL). The combined extracts were washed with saturated brine, dried (MgSO4). After filtration, methylene chloride was removed using a rotary evaporator. The residue was purified by column chromatography over silica gel, eluting with 10% ethyl acetate in methylene chloride. The product was obtained as orange liquid (4.5 g, 82%). 1H NMR δ: 2 (m, 2 H, CH2—CH2—OCOCH3), 2.03 (s, 3 H, CH3), 3.04 (t, 2 H, J=7.2 Hz, S—CH2), 4.15 (t, 2 H, J=6.2 Hz, CH2—OCOCH3), 7.04 (d, 1 H, J=3.9 Hz, aromatic H), 7.59 (d, 1 H, J=3.9 Hz, aromatic H), 9.75 (s, 1 H, CHO); λmax/nm (εmax/dm3 mol−1cm−1) 339 (14,200); HRMS (EI+) calc. for C10H12O3S2: 244.0231. found 244.0228. The product was used without further purification in preparation of 63.

Provenance & Evidence