Diethyl methylmalonate → Methyl-(4-phenoxybutyl)-malonic acid diethyl ester

HRID 1287351Notes

Reaction equation

HRID 1287351 reaction equation
[H][H].[H-].[Na+].[CH2:5]([O:7][C:8](=[O:16])[CH:9]([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:6].[O:17]([CH2:24][CH2:25][CH2:26][CH2:27]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:5]([O:7][C:8](=[O:16])[C:9]([CH3:15])([CH2:27][CH2:26][CH2:25][CH2:24][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH3:6]

Participants

7

Reactant 4

HCID 11857Diethyl methylmalonateHCID 24758Sodium hydrideHCID 70986(4-Bromobutoxy)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 53773953Methyl-(4-phenoxybutyl)-malonic acid diethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

After the development of hydrogen was finished 30 g (1 mol) of a 80% suspension of sodium hydride in mineral oil were added portionwise to 191 g (1.1 mols) of methylmalonic acid diethyl ester in 300 ml of absolute toluene and 50 ml of dry dimethylformamide were added and after that, 252 g (1.1 mols) of 4-phenoxy-1-bromobutane (J.O.C. 27, 1290 (1962) were added. The mixture was refluxed for about 13 hours until the medium had a neutral reaction. It was worked up as in 4 a).

Workup

  1. additionwere added
  2. addition27, 1290 (1962) were added
  3. temperatureThe mixture was refluxed for about 13 hours until the medium
  4. customa neutral reaction

Sources & evidence

ORD record
ord-f6e06d804915421dae9e4e8dda53d021
Source dataset
uspto-grants-1976_10
Patent number
US03984459

Reaction notes

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