Diisopropylamine → HCID 68453297, compound

Participants

Reaction Steps

n-BuLi (4.09 ml, 6.5 mmol, 1.6 M in hexane) was added to a suspension of t-BuOK (735 mg, 6.55 mmol) and diisopropyl amine (926 ul, 6.55 mmol) in THF (20 ml) at −78° C. The mixture was stirred at −78° C. for 15 min. before a solution of bis(1,1-dimethylethyl) [1-(4-biphenylyl)ethyl]imidodicarbonate (2.08 g, 5.24 mmol ) in THF (20 ml) was added dropwise and stirring was continued for 30 min at −78° C. The reaction mixture was diluted with HCl (2M, 50 ml) and the product was extracted with ether (3×30 ml). The ether extracts were concentrated and then purified by silica gel chromatography (120 g Redisep column, silica, 40 um, 60 Å, 85 mL/min, A: hexane, B: ethyl acetate, B: 4% for 2 min, 10% for 30 min, detection at 214 nm) which gave 1.15 g (55%) as a clear oil. 1H NMR(CDCl3): delta 7.38-7.63 (m, 9H, arom), 5.95 (1H), 2.01 (3H), 1.41 (S, 18H)

Provenance & Evidence