Water → 1,4-Diethyl 2-formylbutanedioate

Temperature

40 °C

To a suspension of sodium (333 mg, 14 mmol, 1.2 eq) in diethyl ether (7 mL) were added succinic acid diethyl ester (2.1 g, 12 mmol, 1 eq) and formic acid ethyl ester (1.7 mL, 20 mmol, 1.7 eq). The mixture was stirred at 40° C. for 5 h. Water (10 mL) was added and the aqueous layer was washed with diethyl ether (2×10 mL). The aqueous layer was then acidified with a 6N solution of hydrochloric acid and extracted with diethyl ether (3×10 mL). The organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo to afford the expected compound as orange oil (2.6 g, quant. yield).

1. washthe aqueous layer was washed with diethyl ether (2×10 mL)
2. extractionextracted with diethyl ether (3×10 mL)
3. dry with materialThe organic layers were dried over magnesium sulfate
4. filtrationfiltered
5. customevaporated in vacuo

ORD record

ord-2af018deacdc422e955be1e741a90177

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434745B2