Iodine → HCID 68721847, compound

HRID 885122Notes

Reaction equation

HRID 885122 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.[C:7]1(=[O:12])[CH2:11][CH2:10][CH2:9][CH2:8]1.C([Li])CCC.[I:18]I>O1CCCC1.CCCCCC>[I:18][C:6]1[S:5][C:4]([C:7]2([OH:12])[CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:3][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 807IodineHCID 8452CyclopentanoneHCID 127484-MethylthiazoleHCID 178418339Butyllithium

Product 1

HCID 68721847HCID 68721847, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a cold (−78° C.) solution of 4-methylthiazole (2.0 mL, 20.2 mmol) in tetrahydrofuran (130 mL) was added w-butyllithium (8.10 mL, 20.2 mmol, 2.48 M in hexane) dropwise. After 15 minutes, cyclopentanone (1.79 mL, 20.2 mmol) was added in a single portion. After 30 minutes, n-butyllithium (8.10 mL, 20.2 mmol, 2.48 M in hexane) was added dropwise. The reaction was allowed to stir for an additional 20 minutes, after which a solution of iodine (5.13 g, 20.2 mmol) in tetrahydrofuran (15 mL) was added dropwise. The reaction was then quenched by the addition of saturated aqueous Na2S2O3 and ethyl acetate (1.0.0 mL) and allowed to warm to ambient temperature. The layers were separated, and the aqueous was extracted with additional ethyl acetate (2×100 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated to give a dark solid. Trituration of the residue, with hexane gave the title compound as a beige solid. MS (ESI) m/z 310[M+H]+.

Workup

  1. waitAfter 30 minutes
  2. customThe reaction was then quenched by the addition of saturated aqueous Na2S2O3 and ethyl acetate (1.0.0 mL)
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with additional ethyl acetate (2×100 mL)
  5. dry with materialThe combined organics were dried with anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a dark solid

Sources & evidence

ORD record
ord-e23cfe6951c24ab9813de3a5b317158c
Source dataset
uspto-grants-2012_08
Patent number
US08242139B2

Reaction notes

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