Water → HCID 66682498, 화합물

HRID 1964500노트

반응식

HRID 1964500 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 66682498HCID 66682498, 화합물수율 65.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-383a43e5456842559ba2bf49869431e9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415359B2

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