Benzene → Dibenzyl ethylmalonate

Reaktionsgleichung

[CH2:1]([CH:3]([C:7]([OH:9])=[O:8])[C:4]([OH:6])=[O:5])[CH3:2].N12CCCN=[C:16]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH:29]1C=CC=CC=1>>[CH2:1]([CH:3]([C:7]([O:9][CH2:29][C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:8])[C:4]([O:6][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5])[CH3:2]

Komponenten

Edukt 4

HCID 241Benzene

HCID 7498Benzyl Bromide

HCID 11756Ethylmalonic acid

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Produkt 1

HCID 53752489Dibenzyl ethylmalonate

Versuchsvorschrift

A solution of 2.0 g (15 mmol) of ethyl-malonic acid, 4.7 mL (31 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 3.9 mL (32 mmol) of benzyl bromide in 100 mL of benzene was refluxed for 22 hours. After cooling, the reaction was washed with 150 mL of H2O. After separating layers, the organic phase was dried over MgSO4 and concentrated. The residue was purified on a 40M Biotage column using 24:1 v/v hexane/EtOAc as the eluant to afford the title compound as a colorless oil: RF: 0.40 (9:1 v/v hexane/EtOAc); 1H-NMR (500 MHz) δ 0.97 (t, J=7.4, 3H), 1.99 (quint, J=7.4, 2H), 3.39 (t, J=7.4, 1H), 5.17 (s, 2H), 7.29–7.36 (m, 10H).