Iodoethane → HCID 58959918, compound

HRID 916008Notes

Reaction equation

HRID 916008 reaction equation
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:5][C:6]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:7][C:8]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[OH:18])([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].I[CH2:39][CH3:40]>CN(C=O)C.[Cl-].[Na+].O>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:26]=1)[CH2:5][C:6]([OH:23])([CH2:7][C:8]([C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[O:18][CH2:39][CH3:40])([CH3:10])[CH3:9])[C:19]([F:21])([F:22])[F:20]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 58959988HCID 58959988, compound

Product 1

HCID 58959918HCID 58959918, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the 34 mg (0.071 mmol) of 2-[3-(3-chloro-2-fluoro-5-trifluoromethylbenzyl)-4,4,4-trifluoro-3-hydroxy-1,1-dimethylbutyl]-4-fluorophenol in 0.5 mL of anhydrous DMF was added 78 mg (0.56 mmol) of potassium carbonate followed by 0.1 mL (1.25 mmol) of iodoethane. The mixture was stirred under argon for 2 hours and was then diluted with brine (4 mL) and extracted with three 5 mL portions of EtOAc. The combined organic layers were washed with three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was dissolved in hexanes and chromatographed on silica gel eluting with hexanes and then EtOAc-hexanes (0.5:99.5) to afford 19.6 mg of the title compound as a oil.

Workup

  1. extractionextracted with three 5 mL portions of EtOAc
  2. washThe combined organic layers were washed with three 5 mL portions of brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude material was dissolved in hexanes
  7. customchromatographed on silica gel eluting with hexanes

Sources & evidence

ORD record
ord-89e421d8feb3448889018c4508833dc7
Source dataset
uspto-grants-2007_09
Patent number
US07268152B2

Reaction notes

Loading…