2-Methoxynaphthalene → 6-Methoxy-2-naphthyl-2-methylsulfonyloxy-1-propanone

HRID 1719369Notes

Reaction equation

HRID 1719369 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[CH3:13][S:14]([O:17][C@@H:18]([CH3:22])[C:19](Cl)=[O:20])(=[O:16])=[O:15]>ClC1C=CC=CC=1Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:19](=[O:20])[CH:18]([O:17][S:14]([CH3:13])(=[O:16])=[O:15])[CH3:22])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 71192-MethoxynaphthaleneHCID 13186836(2S)-1-Chloro-1-oxopropan-2-yl methanesulfonate

Product 1

HCID 132310556-Methoxy-2-naphthyl-2-methylsulfonyloxy-1-propanone

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

791 Mg (5.00 mmols) of β-methoxynaphthalene and 933 mg (5.00 mmols) of (S)-2-(methylsulfonyloxy)propionyl chloride were dissolved in 5 ml of anhydrous o-dichlorobenzene, followed by stirring at room temperature. To the solution was added 296 mg of dry ferric sulfate obtained by drying ferric sulfate heptahydrate at 150° C. for 3 hours in vacuo, and the mixture was stirred at 70° C. for 18 hours under an argon gas stream. 30 Ml of water was added to the mixture, which was then extracted with methylene chloride (30 ml×2). The extract was washed with water (10 ml×2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily residue was purified by column chromatography (silica gel, methylene chloride) to obtain (S)-1-(6-methoxy-2-naphthyl-2-methylsulfonyloxy-1-propanone as a colorless glass-like material having [α]D26 -35.6°(c=0.982, CHCl3). The resulting product was crystallized in methanol and recrystallized from the same solvent to obtain colorless needles having a melting point of 156°-157° C.

Workup

  1. customobtained
  2. dry with materialby drying ferric sulfate heptahydrate at 150° C. for 3 hours in vacuo
  3. stirringthe mixture was stirred at 70° C. for 18 hours under an argon gas stream
  4. addition30 Ml of water was added to the mixture, which
  5. extractionwas then extracted with methylene chloride (30 ml×2)
  6. washThe extract was washed with water (10 ml×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe oily residue was purified by column chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-ed4cb3a086ce45cb814655240c1d836b
Source dataset
uspto-grants-1985_09
Patent number
US04539420

Reaction notes

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