ChemicalBook CAS DataBase List Ethyl 2-(ethoxymethylene)acetoacetate

Ethyl 2-(ethoxymethylene)acetoacetate synthesis

5synthesis methods

Product Name:Ethyl 2-(ethoxymethylene)acetoacetate
CAS Number:3788-94-1
Molecular formula:C9H14O4
Molecular Weight:186.21

Ethyl 2-(ethoxymethylene)acetoacetate is obtained by heating Ethyl Acetoacetate with Triethyl Orthoformate in Acetic Anhydride.

141-97-9 Synthesis

141-97-9
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$5.00/25g

122-51-0 Synthesis

122-51-0
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$10.00/5ml

3788-94-1
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$11.00/1g

Yield:3788-94-1 80%

Reaction Conditions:

with acetic anhydride at 130; for 5 h;

Steps:

2.2.22.a

2.22 Example 22 {prepared via Scheme 12)- 6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-lH-3-benzazepin-7-yl)methyl]-2-(3-methoxyazetidin-l- yl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-5-one . iStep a) Intermediate 25Ethyl 2-(ethoxymethylene)-3-oxobutanoate A solution of ethyl 3-oxobutanoate (20 g, 154 mmol), triethylorthoformate (51.1 ml, 307 mmol), and acetic anhydride (43.5 ml, 461 mmol) was heated at 130 °C for 5 h. The reaction was cooled to r.t. and concentrated under reduced pressure to remove triethyl orthoformate and acetic anhydride. The remainder of acetic anhydride and triethyl orthoformate was removed by distillation (30 mbar, 30-70 °C). Ethyl 2-(ethoxymethylene)-3-oxobutanoate was distilled off (6 mbar, 80 °C to 128 °C) to leave ethyl 2-(ethoxymethylene)-3-oxobutanoate as a viscous yellow oil (22.8 g, 80%) NMR (400 MHz, CDC1₃) δ 7.59 - 7.69 (m, 1H), 4.17 - 4.34 (m, 4H), 2.29 - 2.44 (m, 3H), 1.25 - 1.44 (m, 6H).

References:

WO2011/83316,2011,A1 Location in patent:Page/Page column 52-53