Diethyl ethylmalonate → HCID 178471350, compound

HRID 839323Notes

Reaction equation

HRID 839323 reaction equation
[H-].[Na+].[CH2:3]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].C1(C)C=CC(S(O[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[C:32](=[O:36])[CH2:33][CH2:34][CH:35]=2)(=O)=O)=CC=1.[CH:38]1[C:39](/[CH:54]=[N:55]/[OH:56])=[CH:40][CH:41]=[N+:42]([CH2:44][N+:45]2[CH:50]=[CH:49][C:48](/[CH:51]=[N:52]/[OH:53])=[CH:47][CH:46]=2)[CH:43]=1.[Br-:57].[Br-]>COCCOC>[C:11]([C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH2:3][CH3:4])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]1[C:32](=[O:36])[CH2:33][CH2:34][CH:35]=1)([O:13][CH2:14][CH3:15])=[O:12].[CH:40]1[C:39](/[CH:54]=[N:55]/[OH:56])=[CH:38][CH:43]=[N+:42]([CH2:44][N+:45]2[CH:46]=[CH:47][C:48](/[CH:51]=[N:52]/[OH:53])=[CH:49][CH:50]=2)[CH:41]=1.[Br-:57].[Br-:57]

Participants

5

Reactant 3

HCID 8610Diethyl ethylmalonateHCID 24758Sodium hydrideHCID 178427726HCID 178427726, compound

Product 1

HCID 178471350HCID 178471350, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of diethyl sodio ethylmalonate, prepared from 1.63 g. (0.0387 mole) of sodium hydride in mineral oil (57.2%) and 8.5 g. (0.0452 mole) of diethyl ethylmalonate in 100 ml. of ethylene glycol dimethyl ether, is added 7.5 g. of tosylate from Example 26 in 20 ml. of ethylene glycol dimethyl ether and the mixture is refluxed for 3 hours and then allowed to stand at room temperature for 18 hours under nitrogen atmosphere. The reaction mixture is filtered and most of the solvent is removed. The mixture is partitioned between cold dilute hydrochloric acid and diethyl ether, and the organic phase is washed with water and saturated brine, dried (MgSO4), and evaporated to yield an oil. The excess diethyl ethylmalonate is distilled off under reduced pressure to yield 6.7 g. of a yellow oil. IR (film) 1755, 1728, 1627, 1050, 885 cm-1.

Workup

  1. filtrationThe reaction mixture is filtered and most of the solvent
  2. customis removed
  3. customThe mixture is partitioned between cold dilute hydrochloric acid and diethyl ether
  4. washthe organic phase is washed with water and saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto yield an oil
  8. distillationThe excess diethyl ethylmalonate is distilled off under reduced pressure
  9. customto yield 6.7 g

Sources & evidence

ORD record
ord-4a65ff28b0f94e24a84208184f214d01
Source dataset
uspto-grants-1978_06
Patent number
US04094896

Reaction notes

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