Sodium Bicarbonate → HCID 2723959, compound

Participants

Reaction Conditions

Reaction Steps

The raw product from 76 (65.2 g, 200.0 mmol) is taken up in EtOAc (300 mL). The organic phase is washed with 10% HCl solution (3×50 mL), NaClsat solution (3×50 mL), and a solution of H2O (3×50 mL) and then dried over Na2SO4 and concentrated in a rotary evaporator. Acetyl chloride is added (35.5 mL, 500.0 mmol, 2.5 eq.) in portions to allyl alcohol (300 mL) at 0° C. for 15 min, then the previous raw product is added to the reaction mixture. The reaction mixture is then heated at 70° C. for 2.5 h and then at 40° C. overnight. Monitoring of the reaction by TLC (Chex/EtOAc, 7/3) shows the disappearance of 76 (Rf=0.25) and the presence of a less polar main product (Rf=0.35). The reaction mixture is cooled to 0° C., neutralized by adding NaHCO3 and then filtered on Celite and finally concentrated in a rotary evaporator. The volatile substances are coevaporated with Tol (2×100 mL) to give a yellow oil. The yellow oil is purified by silica gel chromatography (Chex/EtOAc, 8/2→1/1) to give the alcohol 58 in the form of a colorless oil (55 g, 72% starting from commercial L-rhamnose 27).

Provenance & Evidence