Diethyl methylmalonate → HCID 53764332, compound

HRID 543517Notes

Reaction equation

HRID 543517 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[C@@H:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1Br>C(O)C>[CH2:12]([O:11][C:9](=[O:10])[C:3]([CH:19]1[CH2:18][CH2:17][CH:16]=[CH:15]1)([CH3:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:13]

Participants

5

Reactant 3

HCID 11857Diethyl methylmalonateHCID 5360545SodiumHCID 1260146310230-26-9

Product 1

HCID 53764332HCID 53764332, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

52.4 g of sodium, cut into small pieces, was introduced into a three-necked flask equipped with dropping funnel, reflux condenser, and KPG agitator. Under an argon atmosphere, 790 ml of absolute ethanol was added dropwise thereto within 3 hours so that the reaction mixture was boiling vigorously. Within 1.5 hours, 157 g of diethyl methylmalonate was added dropwise to the hot, slightly turbid alcoholate solution. The mixture was agitated for another hour and then 205 g of trans-1,2-dibromocyclopentane was added dropwise within one hour to the cooled-off solution. Thereafter the solution was refluxed for 17 hours. After concentration of the reaction solution on a forced circulation evaporator, the residue was combined with ether and dilute hydrochloric acid, the organic phase was washed neutral with saturated sodium chloride solution, dried over sodium sulfate, and distilled under vacuum, thus obtaining 170 g, bp1.5 90°-105° C.

Workup

  1. additionwas introduced into a three-necked flask
  2. customequipped
  3. temperaturereflux condenser
  4. waitWithin 1.5 hours
  5. temperatureThereafter the solution was refluxed for 17 hours
  6. customAfter concentration of the reaction solution on a forced circulation evaporator
  7. washthe organic phase was washed neutral with saturated sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. distillationdistilled under vacuum
  10. customthus obtaining 170 g, bp1.5 90°-105° C.

Sources & evidence

ORD record
ord-9a65732f1fb9432e8ab9388951a93e68
Source dataset
uspto-grants-1984_05
Patent number
US04446147

Reaction notes

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