Triethylamine → 3-Methyl-6-(methylsulfonyl)naphthalen-1-ol

HRID 926140Notes

Reaction equation

HRID 926140 reaction equation
Br[C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:8]=2)[C:3]=1[OH:17].C(N(CC)CC)C>[Pd].C(O)C>[CH3:12][C:11]1[CH:2]=[C:3]([OH:17])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 896769962-Bromo-3-methyl-6-(methylsulfonyl)naphthalen-1-ol

Product 1

HCID 896767463-Methyl-6-(methylsulfonyl)naphthalen-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-3-methyl-6-(methylsulfonyl)naphthalen-1-ol (0.500 g, 1.59 mmol), 10% palladium on carbon (0.050 g) and triethylamine (0.331 mL, 2.38 mmol) in ethanol was stirred under a hydrogen atmosphere for 1.5 hours. Celite was added and the mixture was stirred for 10 minutes, filtered through a pad of Celite and the filtrate concentrated. The residue was dissolved in ethyl acetate, washed with dilute HCl/brine, dried (MgSO4), filtered, concentrated, and purified by flash column chromatography (silica gel, 20 to 50% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M−H]− calcd for C12H11O3S: 235.3. Found: 235.2.

Workup

  1. additionCelite was added
  2. stirringthe mixture was stirred for 10 minutes
  3. filtrationfiltered through a pad of Celite
  4. concentrationthe filtrate concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with dilute HCl/brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash column chromatography (silica gel, 20 to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d1db802652da4de5afc800cccc2124a8
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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