Cesium carbonate → Diallyl [4-(tert-butoxycarbonyl)benzyl]{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}malonate

HRID 1920589Notes

Reaction equation

HRID 1920589 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:27]=[CH:26][C:11]([CH2:12][CH:13]([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:29][CH2:30][C:31]1([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:32]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:1]([O:5][C:6]([C:8]1[CH:27]=[CH:26][C:11]([CH2:12][C:13]([CH2:29][CH2:30][C:31]2([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:33][CH2:32]2)([C:20]([O:22][CH2:23][CH:24]=[CH2:25])=[O:21])[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])=[CH:10][CH:9]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 57965757Diallyl [4-(tert-butoxycarbonyl)benzyl]malonateHCID 57965767Ethyl [1-(2-bromoethyl)cyclopropyl]acetate

Product 1

HCID 57965749Diallyl [4-(tert-butoxycarbonyl)benzyl]{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}malonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 19.85 g (43.4 mmol, purity 81.85%) of diallyl [4-(tert-butoxycarbonyl)benzyl]-malonate, 13.94 g (47.7 mmol, purity 80.5%) of ethyl [1-(2-bromoethyl)cyclopropyl]acetate and 28.56 g (87 mmol) of cesium carbonate in 310 ml of acetonitrile is stirred under reflux for 24 hours. The reaction mixture is then filtered, and the filtrate is concentrated to dryness. The crude product is purified by flash chromatography (3000 g of silica gel 60, mobile phase: cyclohexane/ethyl acetate 20:1). This gives 8 g (35% of theory) of the title compound in the form of a colorless oil.

Workup

  1. temperatureunder reflux for 24 hours
  2. filtrationThe reaction mixture is then filtered
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe crude product is purified by flash chromatography (3000 g of silica gel 60, mobile phase: cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-f866d0aa2def4348adc524588477a72d
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

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