Potassium Iodide → HCID 54555519, compound

HRID 1824331Notes

Reaction equation

HRID 1824331 reaction equation
[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.Br[CH2:32][CH2:33][CH2:34][C:35]#[N:36].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[OH:1][C@@H:2]([CH2:18][N:19]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:32][CH2:33][CH2:34][C:35]#[N:36])=[CH:26][CH:25]=1)[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 54420518HCID 54420518, compound

Product 1

HCID 54555519HCID 54555519, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of the phenol prepared in example 91 (0.90 g, 2.2 mmol), 4-bromobutyronitrile (0.5 mL, 5.0 mmol), potassium carbonate (0.97 g, 7.0 mmol), potassium iodide (0.1 g) and methyl ethyl ketone (30 mL) was heated at reflux for 10 h. The reaction was concentrated in vacuo and the resulting residue partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc (3×). The combined organic layers were washed with water (3×), brine, dried (MgSO4), and concentrated in vacuo to a light pink oil. The material was purified by flash chromatography over silica gel eluting with 5% MeOH/CHCl3 to provide 0.79 g (76%) of a clear oil. MS (FD+) 471.65. NMR.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 h
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe resulting residue partitioned between EtOAc and water
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with EtOAc (3×)
  7. washThe combined organic layers were washed with water (3×), brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo to a light pink oil
  10. customThe material was purified by flash chromatography over silica gel eluting with 5% MeOH/CHCl3

Sources & evidence

ORD record
ord-48b0d9461283440d81c237e4255622a0
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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