Diethyl methylmalonate → (+/-)-2-(2-(2-Naphthyl)benzyl)propionic acid
Reaction equation
[CH3:1][CH:2]([C:8](OCC)=O)[C:3]([O:5]CC)=[O:4].[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1CBr>O.[Na]>[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:8][CH:2]([CH3:1])[C:3]([OH:5])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 130 °C
Procedure
70 g (0.37 mmol) of diethyl methylmalonate dissolved in 50 cm3 of H2O-free EtOH were added dropwise at room temperature to 8.5 g (0.37 mmol) of sodium in 100 cm3 of H2O-free EtOH. 110 g (0.37 mmol) of 26 in 200 cm3 of H2O-free EtOH were subsequently added dropwise, and the mixture was refluxed for 3 hours. 62 g (1.1 mol) of KOB dissolved in 100 cm3 of H2O were added at room temperature, and the mixture was refluxed for a further 4 hours. The solvent was removed in vacuo, H2O was added to the residue until the latter had dissolved completely, and the mixture was acidified to pH 1 by means of concentrated aqueous HCl. The precipitate which had formed was filtered off with suction, dried and heated at 130° C. for 1 hour, giving 90 g (84%) of 27 as a viscous oil.
Workup
- temperaturethe mixture was refluxed for 3 hours
- additionwere added at room temperature
- temperaturethe mixture was refluxed for a further 4 hours
- customThe solvent was removed in vacuo, H2O
- additionwas added to the residue until the latter
- dissolutionhad dissolved completely
- customThe precipitate which had formed
- filtrationwas filtered off with suction
- customdried
Sources & evidence
- ORD record
- ord-83a173e412c047fb87c7286b7145c66d
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840644
Reaction notes
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