Water → HCID 19599884, compound

HRID 611057Notes

Reaction equation

HRID 611057 reaction equation
[CH2:1]([NH:4][CH2:5][C:6]1[CH:10]=[CH:9][O:8][CH:7]=1)[CH:2]=[CH2:3].Br[CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:1]([N:4]([CH2:5][C:6]1[CH:10]=[CH:9][O:8][CH:7]=1)[CH2:12][CH2:13][OH:14])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 19600254HCID 19600254, compound

Product 1

HCID 19599884HCID 19599884, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6.597 g (48.09 mmol) of N-allyl-3-furylmethylamine and 18.0 g (144 mmol) of 2-bromoethanol in 100 ml of N,N-dimethylformamide, 33.2 g of potassium carbonate was added, followed by overnight stirring at 90° C. The reaction mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1) to yield 2-[allyl-(3-furylmethyl)amino]ethanol.

Workup

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Sources & evidence

ORD record
ord-d0f85c8f0653476f95cfca067a96161f
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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