Potassium Iodide → HCID 118113262, compound

HRID 1485066Notes

Reaction equation

HRID 1485066 reaction equation
[H-].[Na+].[I-].[K+].[CH3:5][C:6]([CH3:10])([CH3:9])[CH2:7][OH:8].Cl[CH2:12][C:13]1[CH:24]=[CH:23][C:16]([C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])=[CH:15][CH:14]=1.[Cl-].[NH4+]>CN(C)C=O.O1CCCC1>[CH3:5][C:6]([CH3:10])([CH3:9])[CH2:7][O:8][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])=[CH:23][CH:24]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6404Neopentyl alcoholHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 43627730HCID 43627730, compound

Product 1

HCID 118113262HCID 118113262, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 286 mg) in N,N-dimethylformamide (23.4 mL), a solution of potassium iodide (70.2 mg) and 2,2-dimethyl-1-propanol (618 mg) in N,N-dimethylformamide (5.00 mL) were added. After stirring the mixture at room temperature for an hour, a solution in tetrahydrofuran (5.00 mL) of the compound (1.00 g) obtained in step (1) above was added. After stirring the mixture at room temperature for 3 hours, a saturated aqueous solution of ammonium chloride was added. Two extractions were conducted with a liquid mixture of n-hexane/ethyl acetate (1:1) and the combined organic layers were washed with saturated brine. After drying over anhydrous magnesium sulfate, the desiccant was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-65:35) to give 4-[(2,2-dimethylpropoxy)methyl]-N-methoxy-N-methylbenzamide as a colorless oil (304 mg).

Workup

  1. stirringAfter stirring the mixture at room temperature for 3 hours
  2. extractionTwo extractions
  3. additionwere conducted with a liquid mixture of n-hexane/ethyl acetate (1:1)
  4. washthe combined organic layers were washed with saturated brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe desiccant was removed by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=100:0-65:35)

Sources & evidence

ORD record
ord-e855f9abb8e64535af324bb50c7f56b4
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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