Propargyl bromide → HCID 54171516, compound

HRID 1602398Notes

Reaction equation

HRID 1602398 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[OH:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][NH:15][C:16]([CH:18]2[CH2:20][CH2:19]2)=[O:17])[CH:9]=[CH:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][NH:15][C:16]([CH:18]2[CH2:19][CH2:20]2)=[O:17])[CH:9]=[CH:10][CH:11]=1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 54409627HCID 54409627, compound

Product 1

HCID 54171516HCID 54171516, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Propargyl bromide (80% in toluene, 0.091 ml) was added dropwise to a mixture of cyclopropanecarboxylic acid [3-(3-hydroxy-phenyl)-propyl]-amide (122 mg) and potassium carbonate (154 mg) in dry DMF (10 ml) in an ice bath under nitrogen. The mixture was allowed to warm to room temperature, then heated at 65° C. for 18 h. The cooled mixture was partitioned between water (50 ml) and ethyl acetate (3×15 ml). The combined organic extracts were washed with brine/water 1:1 (3×20 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by column chromatography on silica. Elution with hexane/ethyl acetate 2:1 gave the title compound as a colourless solid (79 mg)

Workup

  1. temperatureheated at 65° C. for 18 h
  2. customThe cooled mixture was partitioned between water (50 ml) and ethyl acetate (3×15 ml)
  3. washThe combined organic extracts were washed with brine/water 1:1 (3×20 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue purified by column chromatography on silica
  7. washElution with hexane/ethyl acetate 2:1

Sources & evidence

ORD record
ord-053873d58632454c9e33b4fff02abf08
Source dataset
uspto-grants-1999_11
Patent number
US05981572

Reaction notes

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