Hydrochloric Acid → HCID 59235946, compound

HRID 1518420Notes

Reaction equation

HRID 1518420 reaction equation
CCCCCC.C([Li])CCC.[CH3:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH:23]=[O:24])[CH:17]=[CH:16]2.[CH3:25][S:26]SC.Cl>C1COCC1>[CH3:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([CH:23]=[O:24])[C:17]([S:26][CH3:25])=[CH:16]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12232Dimethyl DisulfideHCID 64522682-Naphthalenecarboxaldehyde, 6-methyl-HCID 178418244HCID 178418244, compound2×

Product 1

HCID 59235946HCID 59235946, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

A 200 ml three-neck flask equipped with a dropping funnel was heated and dried, and air in the flask was replaced with nitrogen. N,N,N′-trimethyldiamine (1.22 ml, 9.6 mmol) and anhydrous THF (40 ml) were added into the flask and cooled down to −30° C. A butyllithium hexane solution (1.57 M, 6.14 ml, 9.6 mmol) was added thereto and stirred for 15 minutes. The temperature in the flask was brought back to −20° C., and an anhydrous THF (40 ml) solution of 6-methyl-2-naphthaldehyde (1.0 g, 5.9 mmol) was slowly dropped therein and stirred for 15 minutes. Further, after a butyllithium hexane solution (1.57 M, 11.2 ml, 0.017 mol) was added therein and stirred for 3.5 hours, dimethyldisulfide (2.6 ml, 0.029 mol) was added. The temperature was increased to a room temperature, and an obtained solution was stirred for 2 hours. Then, 1 M hydrogen chloride was added to stop the reaction, an obtained reaction solution was extracted with methylene chloride, and an organic layer was dried with anhydrous magnesium and filtrated. A filtrate was concentrated by use of a rotary evaporator. A residue was purified by silica gel column chromatography by use of a mixture solvent of hexane and ethyl acetate (hexane:ethyl acetate=9:1) as a mobile phase, so as to obtain 6-methyl-3-methylthio-2-naphthaldehyde (386 mg, 1.8 mmol, 30%) as a yellow solid.

Workup

  1. customA 200 ml three-neck flask equipped with a dropping funnel
  2. temperaturewas heated
  3. customdried
  4. customwas brought back to −20° C.
  5. stirringstirred for 15 minutes
  6. stirringstirred for 3.5 hours
  7. temperatureThe temperature was increased to a room temperature
  8. stirringan obtained solution was stirred for 2 hours
  9. customthe reaction
  10. customan obtained reaction solution
  11. extractionwas extracted with methylene chloride
  12. dry with materialan organic layer was dried with anhydrous magnesium
  13. filtrationfiltrated
  14. concentrationA filtrate was concentrated by use of a rotary evaporator
  15. customA residue was purified by silica gel column chromatography by use of a mixture solvent of hexane and ethyl acetate (hexane:ethyl acetate=9:1) as a mobile phase

Sources & evidence

ORD record
ord-52ff9b03e0c74012b3f4db1de4952c0e
Source dataset
uspto-grants-2012_07
Patent number
US08232546B2

Reaction notes

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