Water → Diethyl butyl-octylmalonate
Reaction equation
[H-].[Na+].[CH2:3]([CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:5][CH3:6].I[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CS(C)=O>[CH2:3]([C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:5][CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
A mixture of sodium hydride (50% w/w suspension in mineral oil, 2.40 g, 50.0 mmol) in dimethylsulfoxide (50 mL) was cooled to 5° C., and a solution of diethyl butylmalonate (10.0 mL, 45.5 mmol) in dimethylsulfoxide (10 mL) was added dropwise with vigorous stirring. After 4 hours, the solution was treated with iodooctane (8.20 mL, 44.3 mmol), and the solution was stirred an additional 12 hours. It was poured into water (400 mL), and extracted with ethyl acetate (2×500 mL). The extracts were washed in sequence with water (3×400 mL), then saturated brine (400 mL). The extracts were then combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The resulting oil was separated by flash chromatography (3:97 ethyl acetate-hexane) to afford the product, diethyl butyl-octylmalonate, as an oil (13.7 g, 41.7 mmol, 94%).
Workup
- extractionextracted with ethyl acetate (2×500 mL)
- washThe extracts were washed in sequence with water (3×400 mL)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe resulting oil was separated by flash chromatography (3:97 ethyl acetate-hexane)
Sources & evidence
- ORD record
- ord-2228673b075447f58c87348dbce04c3a
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05583147
Reaction notes
Loading…