Propanal → HCID 21862820, compound

HRID 856856Notes

Reaction equation

HRID 856856 reaction equation
[CH:1](=[O:4])[CH2:2][CH3:3].C(NC(C)C)(C)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:23])[CH2:21]Br)=[CH:16][CH:15]=1>O1CCCC1.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH2:21][CH:2]([CH3:3])[CH:1]=[O:4])=[O:23])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 527PropanalHCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 7912Diisopropylamine

Product 1

HCID 21862820HCID 21862820, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4.36 g (75 mmol) of propionaldehyde were added dropwise under a stream of nitrogen to a solution of 6.46 g (50 mmol) of diisopropylamine, 39 g of molecular sieves 4 Å and 10 mg of 2,6-di-t-butyl-4-methylphenol in 50 ml of tetrahydrofuran, and the mixture was left to stand for 3 hours. At the end of this time, 5.73 g (25 mmol) of 4′-methoxy-2-bromoacetophenone were added to the mixture, and the mixture was left to stand at room temperature overnight. The reaction mixture was then filtered, and 55 ml of 1N aqueous hydrochloric acid were added to the filtrate to separate it into liquid phases. The aqueous layer was separated and extracted twice with ethyl acetate. The organic extracts were combined and washed with water and with a saturated aqueous solution of sodium chloride, in that order. The resulting solution was then dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 2:1 by volume mixture of hexane and ethyl acetate, to give 2.82 g (yield 26%) of the title compound as a pale yellow oily substance.

Workup

  1. waitthe mixture was left
  2. waitthe mixture was left
  3. waitto stand at room temperature overnight
  4. filtrationThe reaction mixture was then filtered
  5. addition55 ml of 1N aqueous hydrochloric acid were added to the filtrate
  6. customto separate it into liquid phases
  7. customThe aqueous layer was separated
  8. extractionextracted twice with ethyl acetate
  9. washwashed with water and with a saturated aqueous solution of sodium chloride, in that order
  10. dry with materialThe resulting solution was then dried over anhydrous magnesium sulfate
  11. concentrationconcentrated by evaporation under reduced pressure
  12. customThe residue thus obtained
  13. washeluted with a 2:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-586c98bf51d540a6864359e2e8382d9e
Source dataset
uspto-grants-2006_12
Patent number
USRE039420E1

Reaction notes

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