Methanethiol → HCID 12067529, compound

HRID 1859384Notes

Reaction equation

HRID 1859384 reaction equation
Br[CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=[O:14].O1CCCC1.[Na].[CH3:21][SH:22]>O>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3](=[O:14])[CH:2]([S:22][CH3:21])[CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 878MethanethiolHCID 8028TetrahydrofuranHCID 5360545SodiumHCID 116012912-bromo-6-methoxy-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 12067529HCID 12067529, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After 20 g of 2-bromo-6-methoxy-1-tetralone [synthesized in accordance with procedures described in W. S. Johnson, et al., J. Am. Chem. Soc., vol.66, p.218 to 220 (1944)] was dissolved into 100 ml of tetrahydrofuran, 36.5 g of a 15% aqueous solution of a sodium salt of methylmercaptan was added dropwise thereto. After the stirring for 3 hours at room temperature, the reaction mixture was poured into 300 ml of cold water. An organic layer was extracted with 200 ml of ether, and the ether layer was sequentially washed with a sodium chloride aqueous solution and water. After the ether layer was dried with magnesium sulfate, the solvent was removed by evaporated under vacuum. The residue was dissolved into 320 ml of a mixed solvent of hexane/ethyl acetate (7/1), and silica gel was added thereto for adsorbing impurities. After the silica gel was removed by filtration, the filtrate was concentrate under vacuum to provide 11.06 g of 6-methoxy-2-(methylthio)-1-tetralone (yield: 64%).

Workup

  1. additionwas added dropwise
  2. extractionAn organic layer was extracted with 200 ml of ether
  3. washthe ether layer was sequentially washed with a sodium chloride aqueous solution and water
  4. dry with materialAfter the ether layer was dried with magnesium sulfate
  5. customthe solvent was removed
  6. customby evaporated under vacuum
  7. dissolutionThe residue was dissolved into 320 ml of a mixed solvent of hexane/ethyl acetate (7/1), and silica gel
  8. additionwas added
  9. customAfter the silica gel was removed by filtration
  10. concentrationthe filtrate was concentrate under vacuum

Sources & evidence

ORD record
ord-bf7e468bbc6148c293f2bc0a7aa2abc8
Source dataset
uspto-grants-2003_03
Patent number
US06528232B1

Reaction notes

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