Sodium Hydroxide → HCID 59392446, compound

Participants

Reaction Conditions

Reaction Steps

35 g of (R)-3,4-bisbenzyloxy-5-((R)-1,2-dihydroxyethyl)-5H-furan-2-one (98.2 mmol; 1 eq.) are dissolved in 250 ml of THF under a protective-gas atmosphere, and 3.93 g of sodium hydroxide (98.2 mmol; 1 eq.) are added at 0° C. After 30 min, the 2-benzotriazol-2-yl-4-bromomethylphenol (35.8 g; 117.9 mmol; 1.2 eq.) dissolved in 100 ml of THF is added dropwise, the mixture is stirred at 0° C. for 60 min and at 70° C. for 7 hours. After the reaction solution has been cooled to room temperature, 2 g of Pd/C are added, and the mixture is hydrogenated for 5 hours under a hydrogen atmosphere at 3 bar and 50° C. After filtration through a Celite pad, the solution is neutralised using 2 N HCl solution. The extraction is carried out twice with 250 ml of sat. NaHCO3 solution and 100 ml of sat. NaCl solution. The product is precipitated from the org. phase using 370 ml of heptane.

Provenance & Evidence