Reaction #1973927

Reaction equation

sodium hydride

malonic acid di-tert-butyl ester

sodium hydride

diethyl ether

4

N-(12-Bromododecyl)phthalimide

→

5c

Yield 67.0%

2-(12-phthalimido dodecyl)propane dioic acid di-tert-butyl ester

Yield 67.0%

Solvents

cyclohexane

dimethylformamide

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   workup.STIRRINGthe reaction mixture was further stirred at room temperature for 7 h

Procedure

29.3 mmol (6.56 mL) of malonic acid di-tert-butyl ester and 29.3 mmol (1.28 g) of sodium hydride in mineral oil (55% (w/w)) were reacted in 120 mL of anhydrous dimethylformamide for 50 min at room temperature according to general procedure B2. 45.4 mmol (23.0 g) of 4′ were added to the mixture and the reaction mixture was stirred for 1 h at 75° C. bath temperature and at room temperature o/n. Additional 16.2 mmol (708 mg) of sodium hydride in mineral oil (55% (w/w)) were added and the reaction mixture was further stirred at room temperature for 7 h. The work-up was performed as described (general procedure B) with diethyl ether. Column chromatography (cyclohexane→cyclohexane/acetone 9:1) gave 5c′ with 67% yield.

Source