Tetrabutylammonium Fluoride → 2-Fluoro-3-octyl-6-(4-hydroxyphenyl)pyrazine

HRID 864271Notes

Reaction equation

HRID 864271 reaction equation
[F:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N:6][CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:22][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:18][CH:17]=2)[N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[N:6][CH:5]=[C:4]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 539852142-Fluoro-3-octyl-6-(4-tert-butyldiphenylsilyloxyphenyl)pyrazine

Product 1

HCID 1355744622-Fluoro-3-octyl-6-(4-hydroxyphenyl)pyrazineYield 90.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

11.82 g (21.87 mmol) of 2-fluoro-3-octyl-6-(4-tert-butyldiphenylsilyloxyphenyl)pyrazine and 43.74 ml of a 1 molar solution of tetra-n-butylammonium fluoride in tetrahydrofuran are stirred for 1 hour at room temperature in 140 ml of tetrahydrofuran. The reaction mixture is partitioned between aqueous sodium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, and freed from solvent, and the product is recrystallized from n-hexane. 6.00 g of 2-fluoro-3-octyl-6-(4-hydroxyphenyl) pyrazine are obtained. ##STR25## 4e

Workup

  1. customThe reaction mixture is partitioned between aqueous sodium chloride solution and ether
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe product is recrystallized from n-hexane

Sources & evidence

ORD record
ord-480c40199ca24712bec0bb5c69a965a3
Source dataset
uspto-grants-1996_10
Patent number
US05562859

Reaction notes

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