Nitrogen → HCID 10087791, compound

Participants

Reaction Steps

A 100 mL 2-necked round bottom flask was equipped with a septum, N2 inlet and 2.6 g (7.4 mmol) of the (R)-(-)-methyl acetate of Example O dissolved in 45 mL of dry toluene. The solution was cooled to -78° C. (CO2 /acetone), and 9 mL (9 mmol) of a 1.0M solution of DIBAL-H in toluene was added slowly (5 min.) with stirring. The reaction mixture was stirred for 1 h at -78° C. and poured into a mixture of 100 g of ice and 100 mL of CHCl3. The reaction flask was rinsed with 100 mL of CHCl3 and the mixture was stirred vigorously for 30 min. After separation of the CHCl3 layer, the aqueous phase was washed with 100 mL of CHCl3 (emulsion!) and the combined CHCl3 extracts were washed once with brine 80 mL, dried (Na2SO4) and concentrated leaving 2.3 g (95%) of the title aldehyde as a colorless oil which was not further purified: 1H-NMR (CDCl3)δ9.54 (d, J=2.1 Hz, 1H), 7.63-7.35 (m, 9H), 5.05 (d, J=2.1 Hz, 1H), 0.97 (s, 9H), 0.14 (s, 3H), 0.07 (s, 3H).

Provenance & Evidence