Potassium Iodide → HCID 23501784, compound

HRID 1835592

Reaction equation

HRID 1835592 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][C:5]=1[OH:18])=[O:3].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:27]([C:29]([CH3:36])([CH3:35])[CH2:30][CH2:31][CH2:32][CH2:33]Br)#[N:28]>CN(C)C=O.O>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:2][CH:1]=2)=[O:3])=[C:5]([O:18][CH2:33][CH2:32][CH2:31][CH2:30][C:29]([CH3:36])([C:27]#[N:28])[CH3:35])[CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 3092574'-Benzyloxy-2'-hydroxyacetophenoneHCID 46382156-Bromo-2,2-dimethylhexanenitrile

Product 1

HCID 23501784HCID 23501784, compoundYield 111%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-benzyloxy-2-hydroxyacetophenone (2.45 g), potassium carbonate (3.25 g), potassium iodide (0.42 g), and 5-cyano-5-methyl-1-bromohexane (2.6 g) in dimethylformamide (40 mL) was heated at 90° C. for 22 hours under nitrogen. The slurry was cooled, poured into water (150 mL) and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4), filtered, and concentrated under reduced pressure to an orange oil. This was purified by flash chromatography (ethyl acetate:hexane) to afford the product (2.4 g) as a clear oil. NMR(CDCl3): 1.37, s (6H); 1.64, m (4H); 1.89, m (2H); 2.58, s (3H); 4.03, t (3H); 5.09, s (2H); 6.50, s (1H); 6.58, d (1H); 7.37, m (5 H); 7.81, d (1H). Mass Spec (GC-MS) m/z=365 (M).

Workup

  1. temperatureThe slurry was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to an orange oil
  7. customThis was purified by flash chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-d0a4102658d44d36b5d976d8d75ca7c9
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Linked notes

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