Reaction #1121745

Reaction equation

methyl tert-butyl ether

Water

NaCl

2-(3-methyl-1-nitromethyl-butyl)-malonic acid diethyl ester

water

→

5-methyl-3-nitromethyl-hexanoic acid ethyl ester

Yield 94.8%

Solvents

DMSO

Conditions

Workup

1. 1
   TemperatureAfter complete conversion, the reaction mixture was cooled to 25° C.
2. 2
   Otherto layer separation
3. 3
   WashThe aqueous layer was washed once with 75 mL of methyl tert-butyl ether
4. 4
   Washwashed once with 50 mL of water
5. 5
   OtherThe combined organic layers were dried
6. 6
   Otherthe volatiles were removed under reduced pressure

Procedure

10.0 g (34 mmol) of 2-(3-methyl-1-nitromethyl-butyl)-malonic acid diethyl ester (XII, R1=ethyl) were dissolved in 140 mL of DMSO. Water (10.4 mL) and solid NaCl (14.6 g) were added and the mixture was heated for 6 hours at 150° C. After complete conversion, the reaction mixture was cooled to 25° C. and 150 mL of methyl tert-butyl ether were added. 100 mL of water were added slowly. The heterogeneous mixture was stirred for 5 minutes prior to layer separation. The aqueous layer was washed once with 75 mL of methyl tert-butyl ether. The organic layers were combined and washed once with 50 mL of water. The combined organic layers were dried and the volatiles were removed under reduced pressure to give 7.0 g of 5-methyl-3-nitromethyl-hexanoic acid ethyl ester (VIII, R1=ethyl; 93% yield).

Source