Reaction #1797516

Reaction equation

methyl 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzoate

DIBAL

→

1-(4-tert-Butylphenyl)-3-(4-(hydroxymethyl)phenyl)imidazolidin-2-one

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otherquenched with ml of sat's Rochelle salt solution
2. 2
   OtherThe mixture was partitioned between 100 ml dichloromethane and 50 ml of 1 N NaOH
3. 3
   OtherThe organic layer was separated
4. 4
   Otherdried
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified on ISCO system (5% methanol in dichloromethane)
7. 7
   Otherto give a pure product as a white crystalline (113 mg, 35%)

Procedure

A solution of methyl 4-(3-(4-tert-butylphenyl)-2-oxoimidazolidin-1-yl)benzoate (270 mg, 0.77 mmol) in dichloromethane (50 ml) at −78° C. was treated with ml of 1.0 M DIBAL solution in dichloromethane. The resulting solution was stirred cold for 2 hour, then quenched with ml of sat's Rochelle salt solution. The mixture was partitioned between 100 ml dichloromethane and 50 ml of 1 N NaOH. The organic layer was separated, dried and concentrated. The residue was purified on ISCO system (5% methanol in dichloromethane) to give a pure product as a white crystalline (113 mg, 35%): 1H NMR (400 MHz, CDCl3) δ 7.60 (d, 2H), 7.50 (d, 2H), 7.10 (m, 4H), 4.64 (s, 2H), 4.00 (s, 4H), 1.58 (s, 9H).

Source