ChemicalBook CAS DataBase List Ethyl 4-(benzyloxy)-3-oxobutanoate

Ethyl 4-(benzyloxy)-3-oxobutanoate synthesis

6synthesis methods

Product Name:Ethyl 4-(benzyloxy)-3-oxobutanoate
CAS Number:67354-34-1
Molecular formula:C13H16O4
Molecular Weight:236.26

13176-46-0
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$8.00/250mg

100-51-6 Synthesis

100-51-6
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$5.00/100g

67354-34-1
92 suppliers
$30.00/1g

Yield: 88.5%

Reaction Conditions:

Stage #1:benzyl alcohol with sodium hydride in tetrahydrofuran at 0; for 0.5 h;Inert atmosphere;
Stage #2:4-bromoethyl acetoacetate in tetrahydrofuran at 20; for 12 h;

Steps:

1a
10149] To a stirred solution ofNaH (21.8 g, 912 mmol 3.0eq.) in THF (300 mL) was added BnOH (32.8 g, 304.0 mmol1.0 eq.) under a N2 atmosphere at 00 C. Afier addition, themixture was stirred for 30 mi Compound A (63.5 g, 304.0mmol 1.0 eq.) was added portionwise. The mixture wasallowed to warm to ambient temperature and stirred foranother 12 h. The reaction was monitored by TLC (petroleumether(PE):EtOAc=5:1). The mixture was poured into 2M HC1solution to .-pH 6. The solution was exacted with EtOAc (200mLx3). The combined organic phases were dried overNa2504, filtered and concentrated. The residue was purifiedby column chromatography on silica gel (PE:EtOAc=30: ito5:i)to give compoundB as a colorless oil (46 g, 88.5%). ‘HNMR (CDC13) ? 7.39-7.29 (m, 5H), 4.59 (s, 2H), 4.17-4.24(q, 2H), 4.14 (s, 2H), 3.53 (s, 2H), 1.31-1.22 (t, 3H).

References:

Hendricks, Robert Than;Beigelman, Leonid;Smith, David Bernard;Stoycheva, Antitsa Dimitrova US2015/72982, 2015, A1 Location in patent:Paragraph 0148; 0149

638-07-3 Synthesis