Nitrogen → N-Triisopropylsilylpyrrole

HRID 1399937Notes

Reaction equation

HRID 1399937 reaction equation
[Li]CCCC.[NH:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.N#N.Cl[Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16]>C1COCC1.O>[CH:15]([Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[N:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1)([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8027PyrroleHCID 139400Triisopropylsilyl chlorideHCID 178418339Butyllithium

Product 1

HCID 145136N-TriisopropylsilylpyrroleYield 110.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution n-BuLi in THF (2.5 M, 19.6 mL, 49 mmol) was added to a stirred solution of pyrrole (3 g, 44.7 mmol) in anhydrous THF (20 mL) at −78° C. in an N2 atmosphere. Then the mixture was warmed to room temperature and stirred at this temperature for 10 min. The mixture was cooled again to −78° C., and chlorotriisopropylsilane (10.5 g, 44.7 mmol) was added dropwisely with stirring. Then the mixture was warmed to room temperature and stirred for additional 30 min., diluted with water (200 mL), extracted with ether (200 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), dried over Na2SO4, concentrated to give crude 1-(triisopropylsilyl)-1H-pyrrole (11 g, 100%) as a oil. LCMS: 224 [M+1]+. 1H NMR (400 MHz, DMSO-d6) δ 0.98 (m, 18H), 1.40 (m 3H), 6.20 (m, 2H), 6.80 (m, 2H).

Workup

  1. temperatureThe mixture was cooled again to −78° C.
  2. stirringwith stirring
  3. temperatureThen the mixture was warmed to room temperature
  4. stirringstirred for additional 30 min.
  5. extractionextracted with ether (200 mL)
  6. washThe organic layer was washed with water (2×100 mL) and brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-98068dc2adf149d38d18c1eae7ec3e06
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

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