Benzene → Dibenzyl ethylmalonate

HRID 1245562

Reaction equation

HRID 1245562 reaction equation
[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]

Participants

5

Reactant 4

HCID 241BenzeneHCID 7498Benzyl BromideHCID 11756Ethylmalonic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 53752489Dibenzyl ethylmalonate

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-a9ef386b9fb540bf93afcf5cc3ee8541
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Linked notes

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