Water → HCID 66682498、化合物

HRID 1964500ノート

反応式

HRID 1964500 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 66683082HCID 66683082、化合物HCID 178418339Butyllithium

生成物 1

HCID 66682498HCID 66682498、化合物収率 65.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-383a43e5456842559ba2bf49869431e9
出典データセット
uspto-grants-2013_04
特許番号
US08415359B2

反応ノート

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