Sodium borohydride → HCID 14537114, compound
Reaction equation
[CH:1]([CH2:3][CH2:4][CH2:5][C:6]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)=[O:2].[BH4-].[Na+]>CO>[CH3:17][O:16][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[C:6]([CH2:5][CH2:4][CH2:3][CH2:1][OH:2])[CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The starting 2-(3-formylpropyl)-4-methoxy-1-[(tetrahydro-2H-pyran-2-yl)-oxy]naphthalene (0.587 g) is dissolved in 5 ml methanol. This solution is placed under a nitrogen atmosphere and then cooled to 0°-5° C. and solid sodium borohydride (0.10 g) is added in one portion. Vigorous gas evolution ensues and after stirring for 30 min TLC analysis indicates the reduction is complete. The reaction is quenched with saturated aqueous ammonium chloride and then poured into water. The pH is adjusted to 2-3 (10% aqueous sodium bisulfate) and the mixture extracted with ether. The pH of the aqueous phase is raised to 7 (saturated aqueous sodium bicarbonate), excess solid sodium chloride is added and the mixture reequilibrated. The organic extract is dried with magnesium sulfate, filtered and concentrated to give the crude product as an orange colored oil.