Triethyl phosphite → HCID 86627329, compound

Participants

Reaction Steps

A solution of 4.98 g (10.0 mmol) of bromide 4 in 25 mL (150 mmol) of triethyl phosphite [(EtO)3P] was heated at 150° C. (oil bath temperature) overnight. After the excess of (EtO)3P was removed by using a stream of air, the residue was purified by column chromatography on silica gel (elution with CHCl3/MeOH 25:1) to give 4.39 g (79%) of benzoyl phosphonate 5 as a colorless oil; [α]25D −6.88° (c 5.8, CHCl3); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=6.7 Hz), 1.26 (br s, 26H), 1.28-1.33 (m, 6H), 1.70-2.00 (m, 2H), 3.43-3.62 (m, 4H), 4.06-4.12 (m, 4H), 5.23-5.27 (m, 1H), 7.42-7.46 (m, 2H), 7.54-7.59 (m, 1H), 8.04 (d, 2H, J=7.0 Hz); 13C NMR (CDCl3) δ 14.1, 16.4 (d, J=5.8 Hz), 22.2 (d, J=143.2 Hz), 22.6, 24.3 (d, J=4.0 Hz), 29.3, 29.4, 29.6, 29.7, 31.9, 61.6, 71.3, 71.7, 72.8 (d, J=18.1 Hz), 127.7, 128.3, 129.6, 130.1, 133.0, 166.0; MS (electrospray) MH+m/z calcd for C31H56O6P 555.39, found 555.3.

Provenance & Evidence