Dimethylformamide → HCID 11332876, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-methyl-3-trimethylsilyloxy-1-butyne (8.35 g, 53.4 mmol) in THF (200 mL) and cool to 40° C. Add n-butyllithium (26.7 mL of a 2.0 M solution in cyclohexane, 53.4 mmol, 1 eq.) dropwise over a 5 minute period. Stir for 10 min., then add dry DMF (8.27 mL, 7.81 g, 107 mmol, 2 eq.) in one portion. After 30 min., pour into a cooled (0° C.), vigorously stirred mixture of 10% KH2PO4 (290 mL, 213 mmol) and ether (300 mL). Separate the layers and wash the organic layer with water (2×200 mL). Dry (MgSO4), filter, and concentrate to give 9.4 g (94% crude) of a light oil. Use without further purification. TLC: Rf=0.40 (20:1 hexanes/EtOAc); 1H NMR (CDCl3, 300 MHz) δ 9.03 (s, 1H), 1.35 (s, 6H), 0.02 (s, 9H).

Provenance & Evidence