Acetic Acid → HCID 10364955, compound

Participants

Reaction Steps

To 100 mL of dry MeOH was added 0.18 g (7.83 mmol) of sodium metal. After the sodium metal had completely disappeared, a solution of 3.91 g (7.05 mmol) of benzoyl phosphonate 5 in 10 mL of dry MeOH was added. After the mixture was stirred overnight, the reaction was quenched by addition of 500 μL (8.73 mmol) of AcOH and then concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (elution with CHCl3/MeOH 10:1) to provide 2.56 g (86%) of hydroxy phosphonate 6 as a colorless oil; [α]25D −5.20° (c 5.0, C6H6); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=6.8 Hz), 1.26 (br s, 26H), 1.54-1.58 (m, 2H), 1.70-1.90 (m, 4H), 2.78 (br s, 1H), 3.29 (dd, 1H, J=7.1, 9.4 Hz), 3.40-3.48 (m, 3H), 3.74 (d, 6H, J=10.8 Hz), 3.70-3.85 (m, 1H); 13C NMR (CDCl3) δ 14.0, 20.7 (d, J=142.1 Hz), 22.6, 26.0, 26.1 (d, J=4.7 Hz), 29.3, 29.4, 29.5, 29.6, 31.9, 52.3, 69.8 (d, J=14.8 Hz), 71.6, 74.4; MS (electrospray) MH+ m/z calcd for C22H48O5P 423.3, found 423.3.

Provenance & Evidence