Dimethyl Sulfate → HCID 14823627, compound

HRID 2165127Notes

Reaction equation

HRID 2165127 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.O1CCC[CH2:20]1.C([Li])CCC.COS(OC)(=O)=O>C([Li])CCC.O>[CH3:20][C:16]1[S:15][C:14]([C:12]2[S:13][C:9]([C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 230443065-[4-(Methylsulfanyl)phenyl]-2,2'-bithiopheneHCID 178418339Butyllithium

Product 1

HCID 14823627HCID 14823627, compound

Reagents, catalysts & solvents 2

HCID 178418339ButyllithiumCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a stirred solution of 0.82 gram (0.003 mole) of 5-(4-methylthiophenyl)[2,2'-bithienyl] in 100 ml of freshly distilled tetrahydrofuran was cooled to 0° C. and 1.4 ml of n-butyllithium (2.6M in hexanes) was added dropwise via syringe during a ten minute period. Upon completion of addition the reaction mixture stirred at 0° C. for 30 minutes, then at ambient temperature for three hours. The reaction mixture was recooled to 0° C. and an additional five drops of n-butyllithium was added. The reaction mixture stirred at 0° C. for one hour then 0.32 ml (0.0034 mole) of dimethylsulfate was added. Upon completion of addition the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was taken up in 70 ml of water and the organic layer was separated. The aqueous layer was washed with three 25 ml portions of chloroform. The organic layers were combined and washed, first with water, then with an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 0.78 gram of 5'-methyl-5-(4-methylthiophenyl)[2,2'-bithienyl]; m.p. 145°-147° C.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. waitat ambient temperature for three hours
  3. customwas recooled to 0° C.
  4. stirringThe reaction mixture stirred at 0° C. for one hour
  5. additionUpon completion of addition the reaction mixture
  6. stirringwas stirred at ambient temperature for 16 hours
  7. customthe organic layer was separated
  8. washThe aqueous layer was washed with three 25 ml portions of chloroform
  9. washwashed, first with water
  10. dry with materialThe organic layer was dried with sodium sulfate
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4685f86124aa489e8b3d68bb4c4988f1
Source dataset
uspto-grants-1990_07
Patent number
US04939165

Reaction notes

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