Ammonia → HCID 70585385, compound

Participants

Reaction Steps

To liquid ammonia (500 ml) at -78° was added dropwise a solution of 3 (17.20 g, 43 mmol) in toluene (150 ml). To the stirred biphasic system was added sodium (2.94 g, 0.128 g atoms) and the resulting blue solution stirred at -78° for 1 hr. Excess NH4Cl was added to quench the blue color and the ammonia allowed to evaporate at room temperature. The residual suspension was diluted with 5% NaOH and extracted 3 times with ether. Evaporation of the dried organic phase gave 4 as a tan syrup. NMR (CDCl3): δ7.17-6.53; m(3), aromatic; 5.47, d(1), H8, J7,8 =4 Hz; 5.10, s(1), H5α; 3.78, 3.65, 2.43, singlets; 1.23 d(3), 7--CH3, J=7 Hz.

Provenance & Evidence