Hexane → HCID 58730928, compound

Participants

Reaction Conditions

Reaction Steps

To 2.5 M n-BuLi in hexane (0.67 mL, 1.69 mmol) in THF (5 mL), cooled to −78° C., was added a solution of 26 (0.25 g, 0.80 mmol) in THF (1.0 mL) dropwise. The solution was stirred at −78° C. for 10 min then a solution of Bu3SnI (446 mg, 0.96 mmol) in THF (0.5 mL) was added in one portion. The reaction mixture was stirred at −78° C. for 1 h then at room temperature for 2 h, then poured onto a mixture of ethyl acetate/saturated aq. NaHCO3. The aqueous phase was extracted with more ethyl acetate (2×). The combined organic solutions were dried (MgSO4) and concentrated to give stannane 42 as a light orange oil (483 mg, 115%); 1H NMR (400 MHz, CDCl3) δ 0.71 (s, 6H), 0.98 (t, J=7.4 Hz, 9H), 1.02 (s, 9H), 1.15-1.70 (m, 18H), 6.56 (d, J=3.5 Hz, 1H), 7.26 (d, J=3.5 Hz, 1H), 8.01 (d, J=1.4 Hz, 1H), 8.33 (d, J=1.4 Hz, 1H).

Provenance & Evidence