Hydrochloric Acid → 4-Tert-butyl 1-methyl 2-(benzyloxy)-3-oxosuccinate

HRID 1626777Notes

Reaction equation

[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[C:2]([O:4]C)=O.[CH2:12]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Li+].CC([N-]C(C)C)C.Cl>O1CCCC1>[CH2:12]([O:19][CH:20]([C:2](=[O:4])[C:1]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[C:21]([O:23][CH3:24])=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: -40 °C

Procedure

tert-Butyl methyl oxalate (34 g, 210 mmol) and methyl (benzyloxy)acetate (35 g, 190 mmol) were dissolved in tetrahydrofuran (250 mL) and a solution of LDA in tetrahydrofuran prepared at −78° C. was added dropwise under a nitrogen atmosphere, followed by stirring at the same temperature for 3 hours. The temperature of the reaction solution was gradually raised to −40° C., and subsequently hydrochloric acid (2 M, 210 mL) was added, followed by extraction with ethyl acetate. The extract was washed with water and a saturated aqueous sodium chloride solution, followed by drying over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to afford 4-tert-butyl 1-methyl 2-(benzyloxy)-3-oxosuccinate (62 g) as a yellow oil.

Workup

additionwas added dropwise under a nitrogen atmosphere
extractionfollowed by extraction with ethyl acetate
washThe extract was washed with water
dry with materialby drying over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-dc9b84fc4b494285979b30acf96e237f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785462B2

Reaction notes

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