Acetic Acid → Butanedioic acid, ethyloxo-, diethyl ester

Temperature

-75 °C

27.8 mL of lithium diisopropylamide (50.0 mmol, 1.00 eq, 1.8 M in THF/heptane/ethylbenzene) were dissolved in 50 mL of dry THF and an argon atmosphere and cooled to −75° C. 6.64 mL of ethyl butanoate (50.0 mmol, 1.00 eq) were dissolved in 25 mL of dry THF and added to the previous solution at a bath temperature of −60 to −75° C. and stirred for an additional 1 h at a bath temperature of −75° C. 6.92 mL of diethyl ethanedioate (51.0 mmol, 1.02 eq) were dissolved in 25 mL of dry THF and added to the previous solution at a bath temperature of −60 to −75° C. and stirred for an additional 30 min at a bath temperature of −75° C. The mixture was allowed to come to. −20° C., at which temperature 6.47 mL of acetic acid (113.0 mmol, 2.26 eq), followed by 100 mL of water. The mixture was then allowed to come to rt. The separated organic layer was washed, once with water, once with sodium bicarbonate solution and once with brine, before being dried over sodium sulfate and concentrated in vacuo. The crude reaction product was used for the next transformation without any further purification.

1. additionadded to the previous solution at a bath temperature of −60 to −75° C.
2. additionadded to the previous solution at a bath temperature of −60 to −75° C.
3. stirringstirred for an additional 30 min at a bath temperature of −75° C
4. custom−20° C.
5. customto come to rt
6. washThe separated organic layer was washed, once with water, once with sodium bicarbonate solution and once with brine
7. dry with materialbefore being dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. customThe crude reaction product
10. customwas used for the next transformation without any further purification

ORD record

ord-dd4f7900f0464906b4760c8513281d73

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260412B2