Diethyl phosphonomethanol → HCID 86619968, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 31.2 (280 mg, 0.59 mmol) in dichloroethane (5 mL) was added diethyl (hydroxymethyl) phosphonate (0.22 mL, 1.47 mmol) and pyridinium p-toluene sulfonate (56 mg, 0.29 mmol). The mixture was heated to 60° C. for 1 h and then concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 10% MeOH in CH2Cl2 to give compound 31.3 (102 mg, 16% yield). 1H NMR (300 MHz, CDCl3): δ −0.45 (s, 3H), −0.08 (s, 3H), 0.05 (s, 3H), 0.71 (s, 9H), 0.98 (s, 9H), 1.35 (m, 6H), 1.61 (s, 3H), 3.78 (t, 1H), 3.95 (t, 1H), 4.04 (s, 1H), 4.21 (m, 4H), 4.96 (m, 1H), 6.24 (d, 1H, J=6.7), 8.10 (s, 1H), 8.70 (s, 1H). LRMS (ESI) MH+ C27H52N5O7PSi2 requires 646.9. Found 645.9.

Provenance & Evidence