Sodium Chloride → HCID 136096333, compound

HRID 1780071Notes

Reaction equation

HRID 1780071 reaction equation
[Si]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:30]([Cl: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>[Cl: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 19050001HCID 19050001, compound

Product 1

HCID 136096333HCID 136096333, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4.30 g (8.00 mmol) of 2-(4-tert-butyldiphenylsilyloxyphenyl)-3-chloro-5-octyloxypyridine are stirred at room temperature for 2 hours with 16 ml of a 1-molar tetrabutylammonium fluoride solution in tetrahydrofuran in 50 ml of tetrahydrofuran. Agueous sodium chloride solution is subsequently added, the mixture is extracted with ether, the ether phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and evaporated to dryness, and the product is purified by chromatography (silica gel/hexane:ethyl acetate 8:2), giving 2.16 g of 3-chloro-2-(4-hydroxyphenyl)-5-octyloxypyridine. ##STR32##

Workup

  1. extractionthe 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. customthe product is purified by chromatography (silica gel/hexane:ethyl acetate 8:2)

Sources & evidence

ORD record
ord-a4a286b7e1a449ccb57da1b6b52b08af
Source dataset
uspto-grants-1997_05
Patent number
US05629428

Reaction notes

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