Dabco → HCID 10708760, compound

HRID 555345Notes

Reaction equation

HRID 555345 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)=[O:4].[C:13]([O:17][C:18](=[O:21])[CH:19]=[CH2:20])([CH3:16])([CH3:15])[CH3:14].N12CCN(CC1)CC2>C(OCC)(=O)C.CCCCCC>[C:13]([O:17][C:18](=[O:21])[C:19](=[CH2:20])[CH:9]([OH:10])[C:8]1[CH:11]=[CH:12][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 9237DabcoHCID 15294Methyl 4-FormylbenzoateHCID 15458tert-Butyl acrylate

Product 1

HCID 10708760HCID 10708760, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-(methoxycarbonyl)benzaldehyde (3.3 g, 20 mM), t-butylacrylate (3.5 ml, 24 mM) and 1,4-diazabicyclo[2,2,2]octane (449 mg, 4 mM) were mixed and stirred in a vessel at room temperature for 5 days. The resulting mixture was extracted with ethyl ether. The organic layer was separated, washed with 2N hydrochloric acid, water and an aqueous sodium bicarbonate solution in order, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/19), to obtain 4.1 g of the title compound as a white solid (yield 73%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl ether
  2. customThe organic layer was separated
  3. washwashed with 2N hydrochloric acid, water
  4. dry with materialan aqueous sodium bicarbonate solution in order, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained

Sources & evidence

ORD record
ord-1bb3f1cb47b84416ad2d79f4fa6678ed
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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