Iodoethane → HCID 67205011, compound

HRID 1894318Notes

Reaction equation

HRID 1894318 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[C:10]([OH:11])=[CH:9][C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](I)[CH3:24]>CN(C)C=O.O.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[C:10]([O:11][CH2:23][CH3:24])=[CH:9][C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][CH:6]=1)[CH3:2]

Participants

7

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469765HCID 178469765, compound

Product 1

HCID 67205011HCID 67205011, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-tert-Butyl-4-hydroxy-nicotinic acid ethyl ester (110 mg, 0.5 mmol) was dissolved in dimethylformamide (6 mL). Potassium carbonate was added followed by dropwise addition of ethyl iodine (0.13 mL, 1.5 mmol). The reaction mixture was stirred at room temperature overnight. It was diluted with water and brine and extracted with diethyl ether (2×30 mL). Combined organics washed with brine/water, dried and concentrated to give 6-tert-butyl-4-ethoxy-nicotinic acid ethyl ester as viscous oil (100 mg, 80%). LR-MS: 251 [(M+H)+]

Workup

  1. extractionextracted with diethyl ether (2×30 mL)
  2. washCombined organics washed with brine/water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2607a40e64bd4ba6b10ccc5724155844
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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