4-(benzyloxy)-3-oxobutanenitrile synthesis
- Product Name:4-(benzyloxy)-3-oxobutanenitrile
- CAS Number:118602-96-3
- Molecular formula:C11H11NO2
- Molecular Weight:189.21
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Yield:118602-96-3 31%
Reaction Conditions:
with sodium hydride in tetrahydrofuran;mineral oil at 20 - 50; for 12 h;Inert atmosphere;
Steps:
Synthesis of compound 21
Tetrahydrofuran (1 L) and NaH (30.0 g, 0.77 mol: 60% in mineral oil) were stirred under nitrogen atmosphere and heated to 50°C. To this mixture, a tertahydrofuran solution of compound 23 (135.5 g, 0.70 mol) and acetonitrile (37.1 g, 0.90 mol) were added. The reaction was stirred at room temperature for 12h. The reaction mixture was diluted with water and extracted with MTBE (Methyl tert-butyl ether). The water phase was acidified with citric acid (pH=3) and extracted with ethyl acetate. The organic layer was washed with brine and water, dried over MgSC and concentrated to dryness. The residue was purified by column chromatography (S1O2, c-Hex/AcOEt) to give compound 24 (41 g, yield: 31 %) H-NMR (CDCIs): δ= 7.40- 7.21 (m, 5H), 4.58 (s, 2H), 4.10 (s, 2H), 3.61 (s, 2H).
References:
WO2013/104561,2013,A1 Location in patent:Page/Page column 47
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