Tert-butyl acetoacetate → Methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate

HRID 1732430Notes

Reaction equation

[F-].[K+].[CH3:3][O:4][CH:5]([O:12][CH3:13])/[CH:6]=[CH:7]\[C:8]([O:10][CH3:11])=[O:9].[C:14]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=[O:17]>C(O)(C)(C)C>[C:21]([O:20][C:14]([CH:15]([C:16](=[O:17])[CH3:18])[CH:6]([CH:5]([O:12][CH3:13])[O:4][CH3:3])[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 500-ml reactor are placed 40 g of potassium fluoride, 40 ml of dry tert-butanol, 123 g of methyl cis-4,4-dimethoxy-2-butenate and 36 g of tert-butyl acetoacetate. The mixture is heated at 100° C. with stirring on an oil bath for two days. On completion of the reaction, the tert-butanol is distilled off from the mixture. The residue is dissolved in ethyl acetate, and the solution washed with an aqueous solution of common salt and then dried. The solvent is removed from the product. The resulting residue is purified by a silica gel column and distilled at reduced pressure, giving methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate (compound (7), R1 =t-Bu, R2 =R3 =CH3) in a yield of 95.4%, b.p. 72°-76° C./0.014 mm Hg.

Workup

customInto a 500-ml reactor are placed
customOn completion of the reaction
distillationthe tert-butanol is distilled off from the mixture
dissolutionThe residue is dissolved in ethyl acetate
washthe solution washed with an aqueous solution of common salt
customdried
customThe solvent is removed from the product
customThe resulting residue is purified by a silica gel column
distillationdistilled at reduced pressure

Sources & evidence

ORD record: ord-9025422d3063462b963a43050bf51329
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04237308

Reaction notes

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