Diethyl methylmalonate → HCID 21805819, compound

HRID 1584517Notes

Reaction equation

HRID 1584517 reaction equation
[Na].[CH3:2][CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1>C(O)C>[CH3:2][C:3]([CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1)([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 11857Diethyl methylmalonateHCID 703202-BromomethylnaphthaleneHCID 5360545Sodium

Product 1

HCID 21805819HCID 21805819, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

5.15 g (224 mmol) of sodium were dissolved in 150 ml of absolute ethanol, while heating, and 37.3 ml (217 mmol) of diethyl methylmalonate were added at room temperature. A solution of 50 g (217 mmol) of 2-bromomethylnaphthalene (96% pure) in 270 ml of ethanol was slowly added dropwise at 0° C., and the mixture was heated under reflux for a further 4 to 5 hours. It was poured onto ice-water and extracted with ethyl acetate. The combined organic phases were dried with sodium sulfate and evaporated. After drying under an oil pump vacuum, the oily residue was stirred with hexane at 0° C., whereupon 55 g (81%) of the compound 1 crystallized.

Workup

  1. temperaturewhile heating
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for a further 4 to 5 hours
  4. additionIt was poured onto ice-water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried with sodium sulfate
  7. customevaporated
  8. customAfter drying under an oil pump vacuum
  9. customcrystallized

Sources & evidence

ORD record
ord-a381990079334048833e61cabf31618b
Source dataset
uspto-grants-1999_08
Patent number
US05932669

Reaction notes

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