Diethyl Malonate → HCID 58494029, compound

HRID 1942692Notes

Reaction equation

HRID 1942692 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[C:16]=1[CH2:22][CH3:23]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([Br:14])[C:16]=1[CH2:22][CH3:23])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 21650978HCID 21650978, compound

Product 1

HCID 58494029HCID 58494029, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of malonic acid diethyl ester (24.72 g, 154.36 mmol) in dioxane (400 mL) was added sodium hydride (6.17 g, 60%, 154.36 mmol). The mixture was stirred for 15 minutes. Then 1-bromo-2-ethyl-3-iodo-benzene (D126) (40 g, 128.63 mmol) and cuprous bromide (22.13 g, 154.36 mmol) was added. The reaction mixture was refluxed for 10 hr, and then filtered. The filtrate was concentrated in vacuo to give the crude product, which purified by column chromatography to afford 2-(3-bromo-2-ethyl-phenyl)-malonic acid diethyl ester (D127) (20 g). δH (CDCl3-d6, 400 MHz): 1.13 (3H, t), 1.26 (6H, q), 2.88 (2H, m), 4.17 (1H, m), 4.93 (1H, s), 6.68 (1H, t), 7.41 (1H, d), 7.51 (1H, d).

Workup

  1. temperatureThe reaction mixture was refluxed for 10 hr
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give the crude product, which
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-4febec1b9877483abb640eb7ad0d3eb0
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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