Diisobutylaluminum hydride → {3-[2-(Methyloxy)ethyl]-1-naphthalenyl}methanol
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([C:15](OC)=[O:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 3-[2-(methyloxy)ethyl]-1-naphthalenecarboxylate (1 eq.) from the previous step was taken up in toluene (0.1 M). To this solution was then added DIBAl-H (1.5 M toluene solution, 2.4 eq.) and the resulting solution was vigorously stirred at RT for 4 h. The reaction mixture thus obtained was quenched with 1 N aq. HCl and extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a colorless oil.