Malonic Ester Synthesis

malonic ester synthesis (reactant)

diethyl malonate

diethyl malonate

EtO-CO-CH2-CO-OEt

malonic ester synthesis (types)

adds 1 or 2 R groups

malonic ester synthesis (1R - reagent)

1. NaOEt, EtOH
2. RX
3. Hydrolyze/Decarboxylyze

malonic ester synthesis (2R - reagent)

1. NaOEt, EtOH
2. RX
3. KOt-Bu, EtOH
4. RX
5. Hydrolyze/Decarboxylyze

malonic ester synthesis (1R - product)

1. replaces ester (CO2Et) with R
2. replaces ethyl with H

malonic ester synthesis (2R - product)

1. replaces ester (CO2Et) and an alpha H with 2 R groups
2. replaces ethyl with H

Hydrolyze/Decarboxylyze (reagent steps)

Saponify Acidify Carboxylic acid Heat Decarboxylate (SAC'D)

Hydrolyze/Decarboxylyze (reagents)

1. -OH, H2O
2. H3O+
3. Heat

malonic ester synthesis (1R - steps)

1. alpha C deprotonation by -OEt
2. -C attacks R of RX
3. hydrolyze: Et of both esters replaced with H
4. heat: CO2 deleted

malonic ester synthesis (2R - steps)

1. alpha C deprotonation by -OEt
2. -C attacks R of RX
3. alpha C deprotonation by -OEt
4. -C attacks R of RX
5. hydrolyze: Et of both esters replaced with H
6. heat: CO2 deleted

XRX

causes attachment to alpha C at both Xs