Benzene → Dibenzyl ethylmalonate

HRID 1245562

Reaktionsgleichung

Reaktionsgleichung von HRID 1245562
[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

5

Edukt 4

HCID 241BenzeneHCID 7498Benzyl BromideHCID 11756Ethylmalonic acidHCID 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).

Aufarbeitung

  1. temperatureAfter cooling
  2. washthe reaction was washed with 150 mL of H2O
  3. customAfter separating layers
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on a 40M Biotage column

Quellen und Nachweise

ORD-Eintrag
ord-a9ef386b9fb540bf93afcf5cc3ee8541
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125887B2

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