Diethyl methylmalonate → HCID 18938223, compound

HRID 357676Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

104 g (0.6 mol) of diethyl methylmalonate were added dropwise at room temperature to 13.8 g (0.6 mol) of sodium in 300 cm3 of H2 O-free EtOH. Subsequently, 178 g (0.6 mol) of 2-(3-quinolyl)benzyl bromide were added dropwise and the mixture was heated under reflux for 3 hours. At room temperature, 100 g (1.8 mol) of KOH dissolved in 400 cm3 of H2O were added and the mixture was heated under reflux for a further 4 hours. The EtOH was distilled off and the residue was admixed with H2O until completely dissolved and subsequently acidified with concentrated aqueous HCl to a pH of 1. The precipitate formed was filtered off with suction, dried and heated for 1 hour at 130° C. This gave 145 g (83%) of 2-(2-(3-quinolyl)benzyl)propionic acid as solid.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 3 hours
additionwere added
temperaturethe mixture was heated
temperatureunder reflux for a further 4 hours
distillationThe EtOH was distilled off
dissolutionuntil completely dissolved
customThe precipitate formed
filtrationwas filtered off with suction
customdried

Sources & evidence

ORD record: ord-eb5cceb6f8974693aec17c27e26c6e55
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840947

Reaction notes

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