Sodium borohydride → 1,4-Di-[(methanesulfonyl)oxy]-2-(hydroxymethyl)benzene
Reaction equation
[CH3:1][S:2]([O:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:7]=1[CH:8]=[O:9])(=[O:4])=[O:3].[BH4-].[Na+]>C1COCC1.C(O)C>[CH3:1][S:2]([O:5][C:6]1[CH:13]=[CH:12][C:11]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][C:7]=1[CH2:8][OH:9])(=[O:3])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the product from Step A (17.13 g, 58.2 mmol) in 150 mL of 2:1 THF/ethanol at 0° C. was added sodium borohydride (2.27 g, 60.0 mmol). After 30 minutes, the reaction was carefully quenched by the addition oc saturated NH4Cl solution, then partitioned between EtOAc and saturated NaHCO3 solution. The organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a yellow oil which was used without further purification.