Benzaldehyde → HCID 2840585, compound

HRID 1649549Notes

Reaction equation

HRID 1649549 reaction equation
C([Mg]Br)C.[Mg].C(Br)C.[CH2:9]([N:11]([CH2:14][C:15]#[CH:16])[CH2:12][CH3:13])[CH3:10].[CH:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC.O1CCCC1.C(OCC)(=O)C.O>[C:18]1([CH:17]([OH:24])[C:16]#[C:15][CH2:14][N:11]([CH2:12][CH3:13])[CH2:9][CH3:10])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

10

Reactant 5

HCID 240BenzaldehydeHCID 6332Ethyl BromideHCID 20010DietylaminopropinHCID 5462224MagnesiumHCID 178418443HCID 178418443, compound

Product 1

HCID 2840585HCID 2840585, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl magnesium bromide in anhydrous ether, prepared from magnesium (584 mg) in ether (25 ml) and ethyl bromide (3.00 g) in ether (5 ml) in a conventional manner, was added a solution of N,N-diethyl propargylamine (2.70 g) in anhydrous tetrahydrofuran (8 ml) with stirring at room temperature, and the resulting mixture was stirred under reflux for 30 minutes. To the resulting solution was added dropwise a solution of benzaldehyde (2.54 g) in anhydrous tetrahydrofuran (7 ml) at a temperature below 10° C., and the mixture was stirred at room temperature for 2 hours. The cooled reaction mixture was diluted with ethyl acetate (50 ml), and water was added thereto in order to decompose metal complexes. The reaction mixture was dried over sodium sulfate and filtered. The filtrate was evaporated and chromatographed to afford N-(4-phenyl-4-hydroxy-2-butynyl)-N,N-diethylamine, b.p., 134°-137° C./0.12 mmHg. M.P., 52°-53.5° C.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureunder reflux for 30 minutes
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. customThe cooled reaction mixture
  5. additionwas added
  6. dry with materialThe reaction mixture was dried over sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated
  9. customchromatographed

Sources & evidence

ORD record
ord-151cd8d709454560b54c29d69766695b
Source dataset
uspto-grants-1983_11
Patent number
US04418079

Reaction notes

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