5-METHOXY-3-OXOVALERIC ACID METHYL ESTER synthesis
- Product Name:5-METHOXY-3-OXOVALERIC ACID METHYL ESTER
- CAS Number:62462-05-9
- Molecular formula:C7H12O4
- Molecular Weight:160.17
2544-06-1
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Yield: 87%
Reaction Conditions:
Stage #1:3-Methoxypropionic acid with 1,1'-carbonyldiimidazole in acetonitrile at 20; for 1.5 h;
Stage #2:monomethyl monopotassium malonate with magnesium chloride in acetonitrile at 20;
Steps:
X X. Methyl 5-methoxy-3-oxopentanoate
X. Methyl 5-methoxy-3-oxopentanoate CDl (3.24 g, 20.0 mmol) was added portionwise to a stirred suspension of 3-methoxypropanoic acid (1.81 mi, 19.2 mmol) in anhydrous MeCN (80 mL). The mixture was allowed to stir at rt for 1.5 hrs. A powdered mixture of magnesium chloride (1.57 g, 16.5 mmol) and methyl potassium maionate (4.5 g, 28.8 mmol) was added portionwise (note CO2 gas evolved). The mixture was allowed to stir at rt. Volatiies were removed in vacuo and hydrochloric acid (2M, 105 mL) was added. The solution was stirred at rt for 1 hr and extracted with DCM (3 x 100 mL). The organics were dried over magnesium sulfate, filtered and solvent removed in vacuo to afford methyl 5-methoxy-3-oxopentanoate (2.69 g, 87% yield).
References:
KALVISTA PHARMACEUTICALS LIMITED;SMITH, Alun John;NOVAK, Andrew Richard;EVANS, David Michael;EDWARDS, Hannah Joy;STOCKS, Michael John;DAVIE, Rebecca Louise;MARSH, Sally Louise;HODGSON, Simon Teanby WO2016/83816, 2016, A1 Location in patent:Page/Page column 46
4244-59-1
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![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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62462-05-9
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62462-05-9
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