Water → HCID 20203616, compound
Reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]=1[CH:18]=[O:19].[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:3]=1[CH2:18][OH:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 16 g 4-chloro-3-formyl-flav-3-ene in 500 ml dry methanol at room temperature is added 0.5 g sodium borohydride in small portions. After the addition is completed 500 ml water is added. The solution is filtered and extracted with chloroform. The combined organic extracts are dried over magnesium sulfate and evaporated. Chromatographically pure 4-chloro-3-hydroxymethyl-flav-3-ene is obtained as a yellowish oil; TLC (SiO2, CHCl3): 1 spot, RF 0.18.