Dimethylformamide → HCID 18509522, compound

HRID 1356793Notes

Reaction equation

HRID 1356793 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:5]CN.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:19][CH:20]=[CH:21][C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25].[CH3:28][N:29](C)C=O>>[CH3:25][C:24]([CH3:27])([CH3:26])[C:23]#[C:22]/[CH:21]=[CH:20]/[CH2:19][N:29]([CH2:5][C:4]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:2]([Br:1])[CH:3]=1)[CH3:28]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 10340Sodium CarbonateHCID 18509475HCID 18509475, compoundHCID 454895941-Bromo-6,6-dimethylhept-2-en-4-yne

Product 1

HCID 18509522HCID 18509522, compoundYield 56.3%

Procedure

N-(3-bromo-5-methylbenzyl)methylamine (2.68 g; 12.5 mmol) and sodium carbonate (1.89 g; 17.9 mmol) were added to N,N-dimethylformamide (20 ml). While the mixture was stirred at room temperature, 1-bromo-6,6-dimethyl-2-hepten-4-yne (2.40 g; 11.9 mmol) in N,N-dimethylformamide (15 ml) was added dropwise. The mixture was stirred at room temperature for 1.5 hours, and reaction was stopped by pouring the mixture into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1), to thereby yield 2.24 g of the target compound (yield: 56.3%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1.5 hours
  2. customreaction
  3. additionby pouring the mixture into ice+saturated aqueous sodium bicarbonate solution
  4. extractionfollowed by extraction with ethyl acetate (100 ml)
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-ac53f14c254e404caf2043f7cab73109
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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