2-Chlorothiophene → HCID 18656705, compound

HRID 1598009Notes

Reaction equation

HRID 1598009 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.C([Li])CCC.[CH2:12]1[O:15][C@H:13]1[CH3:14]>O1CCCC1>[Cl:1][C:2]1[S:3][C:4]([CH2:12][C@@H:13]([OH:15])[CH3:14])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 72992-ChlorothiopheneHCID 146262(2S)-2-MethyloxiraneHCID 178418339Butyllithium

Product 1

HCID 18656705HCID 18656705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 2-chlorothiophene (8.17 g) in tetrahydrofuran (80 ml) is cooled to -30° C. and 1.6M n-butyllithium in hexanes (43.0 ml) is added dropwise. The mixture is stirred at -30° C. for about 1 hour, (S)-propylene oxide (4.00 g) is added, and the mixture is warmed to 0° C. and stirred at that temperature for about 3 hours. The reaction is quenched with saturated aqueous ammonium chloride solution, diluted with ether, and the layers separated. The organic layer is washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give the desired product.

Workup

  1. temperaturethe mixture is warmed to 0° C.
  2. stirringstirred at that temperature for about 3 hours
  3. customThe reaction is quenched with saturated aqueous ammonium chloride solution
  4. additiondiluted with ether
  5. customthe layers separated
  6. washThe organic layer is washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3fe852be6764a4eba070879b3a08136
Source dataset
uspto-grants-1998_04
Patent number
US05736554

Reaction notes

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