Sodium borohydride → HCID 21959212, compound
Reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:9][C:8]=1[C:17]1[C:18](=[O:34])[O:19][C:20]2[C:25]([C:26]=1[CH2:27][CH:28]=[O:29])=[CH:24][CH:23]=[C:22]([O:30][CH2:31][O:32][CH3:33])[CH:21]=2>C(O)C>[CH3:3][O:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH2:14][O:15][CH3:16])[CH:10]=[CH:9][C:8]=1[C:17]1[C:18](=[O:34])[O:19][C:20]2[C:25]([C:26]=1[CH2:27][CH2:28][OH:29])=[CH:24][CH:23]=[C:22]([O:30][CH2:31][O:32][CH3:33])[CH:21]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium borohydride (17 mg, 0.45 mmol, 0.5 eq.) was dissolved in ethanol (5 mL), then added into the solution of [3-(2,4-Bis-methoxymethoxy-phenyl)-7-methoxymethoxy-2-oxo-2H-chromen-4-yl]-acetaldehyde (400 mg, 0.90 mmol, 1 eq.) ethanol (10 mL) at −10° C. and the reaction mixture was stirred for 30 minutes. The solvent was evaporated and the resulting residue was dissolved in ethyl acetate (100 mL) and washed twice with brine. The organic layer was dried over anhydrous sodium sulfate then concentrated to yield the crude product which was purified by flash chromatography eluted with 50% ethyl acetate to yield the title compound 3-(2,4-Bis-methoxymethoxy-phenyl)-4-(2-hydroxy-ethyl)-7-methoxymethoxy-chromen-2-one as a solid.