Trimethylsilylacetylene → 2-[4-[2-(Trimethylsilyl)ethynyl]phenyl]pyridine

HRID 1522713노트

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HRID 1522713 반응식
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].I[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:10][CH:9]=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:1][Si:2]([C:5]#[C:6][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:12][CH:13]=1)([CH3:4])[CH3:3]

참가 물질

6

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 69237907HCID 69237907, 화합물

생성물 1

HCID 692372572-[4-[2-(Trimethylsilyl)ethynyl]phenyl]pyridine수율 72%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8471Triethylamine용매

실험 절차

Trimethylsilylacetylene (4.1 mL, 28.8 mmol) and tetrakis(triphenylphosphine)palladium (0) (832 mg, 0.72 mmol) were added to a suspension of (1) (4.06 g, 14.4 mmol) and copper (I) iodide (274 mg, 1.44 mmol) in triethylamine (120 mL) that had been deoxygenated with argon. The mixture was deoxygenated with argon and then stirred under argon at room temperature for 40 hours. Aqueous hydrochloric acid (3 M, 320 mL) and dichloromethane (250 mL) were added. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with aqueous hydrochloric acid (3 M, 30 mL), water (250 mL), brine (250 mL), dried over anhydrous magnesium sulfate, filtered and then the solvent was completely removed. The residue was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:4) as the eluent. The main band was isolated and the solvent completely removed to give (2) (2.59 g, 72%).

후처리

  1. customhad been deoxygenated with argon
  2. customThe mixture was deoxygenated with argon
  3. additionAqueous hydrochloric acid (3 M, 320 mL) and dichloromethane (250 mL) were added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
  6. washThe combined organic layers were washed with aqueous hydrochloric acid (3 M, 30 mL), water (250 mL), brine (250 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was completely removed
  10. customThe residue was purified by column chromatography over silica using a dichloromethane/light petroleum mixture (1:4) as the eluent
  11. customThe main band was isolated
  12. customthe solvent completely removed

출처 및 근거

ORD 기록
ord-1fbf2dd3245e487599b5e80e6bca2a02
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09078330B2

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