ChemicalBook CAS DataBase List 5-METHOXY-3-OXOVALERIC ACID METHYL ESTER

5-METHOXY-3-OXOVALERIC ACID METHYL ESTER synthesis

7synthesis methods

Product Name:5-METHOXY-3-OXOVALERIC ACID METHYL ESTER
CAS Number:62462-05-9
Molecular formula:C7H12O4
Molecular Weight:160.17

2544-06-1

38330-80-2

5-METHOXY-3-OXOVALERIC ACID METHYL ESTER

62462-05-9

1. 3-Methoxypropionic acid (1.81 mL, 19.2 mmol) was suspended in anhydrous acetonitrile (80 mL) and stirred. 2. Methyl 5-methoxy-3-oxopentanoate (3.24 g, 20.0 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 1.5 h. 3. A powdered mixture of magnesium chloride (1.57 g, 16.5 mmol) and potassium methyl malonate (4.5 g, 28.8 mmol) was added in one portion (note that CO2 gas was produced during the reaction). 4. The reaction mixture continued to be stirred at room temperature. 5. MgCl2 (1.57 g, 16.5 mmol) and potassium malonate monohydrate (4.5 g, 28.8 mmol) in a powdered mixture (note that CO2 gas is produced during the reaction). 4. Continue to stir the reaction mixture at room temperature. 5. Vacuum remove the volatiles, then add 2M hydrochloric acid (105 mL). 6. Stir the solution for 1 hour at room temperature, and then extract it with dichloromethane (3 x 100 mL). 7. Combine the organic phases, dry them with MgSO4, filter, and remove the solvents in vacuum. 8. dried, filtered and the solvent was removed in vacuum to afford the target product methyl 5-methoxy-3-oxovalerate (2.69 g, 87% yield).

2544-06-1
116 suppliers
$10.00/1g

38330-80-2 Synthesis

38330-80-2
301 suppliers
$14.00/5g

62462-05-9
81 suppliers
$31.00/100mg

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