4-Methyl-1-p-tolyl-pent-1-en-3-one → trans-4-Methyl-1-p-tolyl-1-penten-3-ol
Reaction equation
[CH3:1][CH:2]([CH3:14])[C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1>CO>[CH3:1][CH:2]([CH3:14])[CH:3]([OH:13])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-methyl-1-p-tolyl-pent-1-en-3-one (77.0 g, 0.41 mol) in methanol (400 mL) was added slowly under argon sodium borohydride (31 g, 0.82 mol). The reaction was stirred at room temperature overnight and methanol (200 mL) was evaporated. The solution was neutralized with hydrochloric acid (2N), extracted with ethyl acetate. The organic layer was successively washed with water, aqueous NaHCO3, water and brine, dried (Mg2SO4), filtered and evaporated to give 80.4 g of trans-4-methyl-1(p-tolyl)-1-penten-3-ol and used without further purification in the next step (step h). 1H NMR (300 MHz; CDCl3): 0.94 (d, J=6.9 Hz, 3 H), 0.99 (d, J=6.6 Hz, 3 H), 1.83 (m, 1 H), 2.33 (s, 3 H), 4.01 (br, 1 H), 6.16 (dd, J1=7.0 Hz, J2=16.0 Hz, 1 H), 6.53 (d, J=16.0 Hz, 1 H), 7.12 (d, J=7.8 Hz, 1 H), 7.28 (d, J=7.8 Hz, 1 H).