Sodium Iodide → HCID 13726886, compound

HRID 1252508Notes

Reaction equation

HRID 1252508 reaction equation
[F:1][CH:2]([F:29])[C:3]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)([CH3:21])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1.[CH2:30](I)[CH3:31].C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>O.CN(C)C=O>[CH2:30]([O:28][C:25]1[CH:24]=[CH:23][C:22]([C:3]([CH3:21])([CH2:4][CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]=2)[CH:2]([F:1])[F:29])=[CH:27][CH:26]=1)[CH3:31]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 13726899HCID 13726899, compound

Product 1

HCID 13726886HCID 13726886, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1.5 g (3.75 mmol) 1,1-difluoro-5-(4-fluoro-3-phenoxyphenyl)-2-(4-hydroxyphenyl)-2-methylpentane, 10 ml dimethylformamide, 700 mg (4.5 mmol) ethyl iodide and 725 mg (5.25 mmol) K2CO3 were heated at 80° C. for 8 hours with a catalytic amount of sodium iodide. It was then added to water, extracted with ethyl acetate, dried over Na2SO4 and evaporated. After chromatography on silica gel, using hexane/toluene, 1.4 g of the desired product remained i.e. 87.4% of theory. The physical data are identical for the product of Example 1. The starting material was obtained as follows

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe starting material was obtained

Sources & evidence

ORD record
ord-8d1d8110271b4b79b1623ef542fc686b
Source dataset
uspto-grants-1988_05
Patent number
US04743622

Reaction notes

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