Diethyl Malonate → HCID 20251324, compound

HRID 1285022Notes

Reaction equation

HRID 1285022 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].I[CH2:15][CH2:16][O:17][CH:18]([O:20][CH2:21][CH2:22]I)[CH3:19]>O1CCCC1>[C:3]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:15][CH2:16][O:17][CH:18]([O:20][CH2:21][CH2:22][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH3:19])([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 18403935HCID 18403935, compound

Product 1

HCID 20251324HCID 20251324, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.28 g (0.11 mol) of sodium hydride was added to 50 ml of dry tetrahydrofuran, and to this solution was added dropwise a mixed solution of 17.6 g (0.11 mol) of diethyl malonate and 10.0 g (0.027 mol) of bis(2-iodoethoxy)ethane, followed by 2-hour reflux under heating. After the reaction, the most part of tetrahydrofuran was distilled off and the residue was added with 10 ml of water, neutralized by adding 1N hydrochloric acid and extracted three times with 50 ml of ether. After drying the extract, ether was distilled off and the oily product was passed through a silica gel packed column and eluted with petroleum ether-ether (4:1) to obtain 7.23 g of bis(3,3-dicarboethoxypropoxy)ethane, (EtO2C)2CHCH2CH2OCH2CH2 -OCH2CH2CH(CO2Et)2 (yield: 60%). The property analyses of this compound showed the following results.

Workup

  1. waitfollowed by 2-hour
  2. temperaturereflux
  3. temperatureunder heating
  4. customAfter the reaction
  5. distillationthe most part of tetrahydrofuran was distilled off
  6. additionthe residue was added with 10 ml of water
  7. additionby adding 1N hydrochloric acid
  8. extractionextracted three times with 50 ml of ether
  9. dry with materialAfter drying the extract, ether
  10. distillationwas distilled off
  11. washeluted with petroleum ether-ether (4:1)

Sources & evidence

ORD record
ord-1a6b7b51d5f044568c982787c5af4d7c
Source dataset
uspto-grants-1986_01
Patent number
US04564690

Reaction notes

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