Sodium Chloride → HCID 135815019, compound

HRID 1757367Notes

Reaction equation

HRID 1757367 reaction equation
[Si]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:30]([F:31])=[CH:29][C:28]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:27][N:26]=2)=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>O1CCCC1>[F:31][C:30]1[C:25]([C:22]2[CH:21]=[CH:20][C:19]([OH:18])=[CH:24][CH:23]=2)=[N:26][CH:27]=[C:28]([O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:29]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 19387548HCID 19387548, compound

Product 1

HCID 135815019HCID 135815019, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.30 g (8.00 mmol) of 2-(4-tert-butyldiphenylsilyloxyphenyl)-3-fluoro-5-octyloxypyridine are stirred for 2 hours at room temperature with 16 ml of a 1-molar tetrabutylammonium fluoride solution in tetrahydrofuran in 50 ml of tetrahydrofuran. Aqueous sodium chloride solution is then added, the reaction mixture is extracted with ether, and the ether phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, evaporated to dryness and purified by chromatography (silica gel/hexane: ethyl acetate 8:2), giving 2.16 g of 3-fluoro-2-(4-hydroxyphenyl)-5-octyloxypyridine. ##STR33##

Workup

  1. extractionthe reaction mixture is extracted with ether
  2. washthe ether phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. custompurified by chromatography (silica gel/hexane: ethyl acetate 8:2)

Sources & evidence

ORD record
ord-bdc54e31a260443aac6effc7ae5149f4
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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