Sodium potassium tartrate tetrahydrate → [6-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanol

HRID 238634Notes

Reaction equation

HRID 238634 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][N:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:27])[CH:11]=2)[CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1>[Br:27][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:3][OH:2])[CH:14]=[C:13]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:23])=[O:24])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21225700DiisobutylaluminumhydrideHCID 593266036-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 59326541[6-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester (280 mg, 0.63 mmol) in tetrahydrofuran (5 mL) was added a solution of diisobutylaluminum hydride (1 M in toluene, 1.3 mL, 1.3 mmol) dropwise at −78° C. under a nitrogen atmosphere. The resulting mixture was warmed to room temperature and stirred at room temperature (the total stirring time between −78° C. and room temperature was 3 hours). The reaction mixture was treated with an aqueous solution of potassium sodium tartrate tetrahydrate at 0° C., warmed to room temperature, and stirred at room temperature for 30 min. The resulting mixture was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether) to give [6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanol (263 mg, 99%) as a colorless oil.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred at room temperature for 30 min
  3. extractionThe resulting mixture was extracted with ethyl acetate (20 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-d4f90def062f47af9dd00947c8559b93
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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