Water → HCID 66682498, compound

HRID 1964500Notes

Reaction equation

HRID 1964500 reaction equation
[CH:1]([Si:4]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[N:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[C:10]1[S:11][CH:12]=[CH:13][N:14]=1)([CH3:3])[CH3:2].[CH2:21]([Li])CCC.IC.O>O1CCCC1>[CH3:21][C:12]1[S:11][C:10]([C:6]2[N:5]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:15]([CH3:17])[CH3:16])[CH:18]([CH3:20])[CH3:19])[CH:9]=[CH:8][CH:7]=2)=[N:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 66683082HCID 66683082, compoundHCID 178418339Butyllithium

Product 1

HCID 66682498HCID 66682498, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[1-(Triisopropylsilyl)-1H-pyrrol-2-yl]-1,3-thiazole (317 mg, 1.03 mmol) synthesized in Example (3a) was dissolved in tetrahydrofuran (10 mL), and cooled to −78° C. n-Butyl lithium (2.64M hexane solution, 0.51 mL, 1.35 mmol) was added dropwise, followed by stirring for 40 minutes, and subsequently iodomethane (0.13 mL, 2.09 mmol) was added and stirring was carried out for 3 hours with the temperature being gradually raised from −78° C. to room temperature. Water (10 mL) was added, and extraction was carried out with diethyl ether (20 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: hexane) to afford the desired compound (215 mg, yield 65%) as a colorless oil.

Workup

  1. additionwas added dropwise
  2. stirringstirring
  3. waitwas carried out for 3 hours with the temperature
  4. temperaturebeing gradually raised from −78° C. to room temperature
  5. extractionextraction
  6. washThe organic layer was washed with saturated brine
  7. dry with materialsubsequently dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified
  10. washsilica gel column chromatography (elution solvent: hexane)

Sources & evidence

ORD record
ord-383a43e5456842559ba2bf49869431e9
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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