Diethyl methylmalonate → (+/-)-2-(2-(2-Naphthyl)benzyl)propionic acid

HRID 1106964Notes

Reaction equation

[CH3:1][CH:2]([C:8](OCC)=O)[C:3]([O:5]CC)=[O:4].[Na].[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1CBr.[OH-].[K+]>O>[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:8][CH:2]([CH3:1])[C:3]([OH:5])=[O:4]

Participants

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. Subsequently, 110 g (0.37 mmol) of 14 in 200 cm3 of H2O-free EtOH were added dropwise and the mixture was heated under reflux for 3 hours. 62 g (1.1 mol) of KOH dissolved in 100 cm3 of H2O were added at room temperature and the mixture was heated under reflux for a further 4 hours. The solvents were removed under reduced pressure, the residue was admixed with H2O until completely dissolved and acidified with concentrated aqueous HCl to a pH of 1. The precipitate formed was filtered off with suction, dried and heated at 130° C. for 1 hour. This gave 90 g (84%) of 15 as a viscous oil.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 3 hours
additionwere added at room temperature
temperaturethe mixture was heated
temperatureunder reflux for a further 4 hours
customThe solvents were removed under reduced pressure
dissolutionuntil completely dissolved
customThe precipitate formed
filtrationwas filtered off with suction
customdried

Sources & evidence

ORD record: ord-34edfe103e174172a763ed084c0b9f89
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057408

Reaction notes

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