Acrolein → HCID 10465389, compound

HRID 1987658Notes

Reaction equation

HRID 1987658 reaction equation
[Li]CCCC.C(NC(C)C)(C)C.[CH2:13]([O:15][C:16](=[O:22])[CH2:17][O:18][CH2:19][CH:20]=[CH2:21])[CH3:14].[CH:23]([CH:25]=[CH2:26])=[O:24]>C1COCC1>[CH2:13]([O:15][C:16](=[O:22])[CH:17]([O:18][CH2:19][CH:20]=[CH2:21])[CH:23]([OH:24])[CH:25]=[CH2:26])[CH3:14]

Participants

6

Reactant 4

HCID 7847AcroleinHCID 7912DiisopropylamineHCID 10630623HCID 10630623, compoundHCID 178418339Butyllithium

Product 1

HCID 10465389HCID 10465389, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of argon, n-BuLi (3 mmol, 1.2 ml, 2.5 M in hexane) was added dropwise to a solution of diisopropylamine (281 mg, 2.78 mmol) in dry THF (20 ml) at −78° C. After stirring for 20-30 min, a solution of allyloxy-acetic acid ethyl ester (200 mg, 1.38 mmol) in THF (4 ml) was added and the mixture was stirred at −78° C. for 10 min. Acrolein (79 mg, 1.38 mmol) was added into the reaction mixture and stirring was maintained until all starting materials were consumed. The reaction was quenched by addition of EtOH (2 ml) and warmed to room temperature. The solution was diluted with EtOAc (60 ml), washed with H2O (20 ml×2), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography with 20% EtOAc-hexane.

Workup

  1. stirringthe mixture was stirred at −78° C. for 10 min
  2. stirringstirring
  3. temperaturewas maintained until all starting materials
  4. customwere consumed
  5. customThe reaction was quenched by addition of EtOH (2 ml)
  6. additionThe solution was diluted with EtOAc (60 ml)
  7. washwashed with H2O (20 ml×2)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography with 20% EtOAc-hexane

Sources & evidence

ORD record
ord-a84021e89b5e4178b3d595f338066b1d
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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