Triethylamine → 1H-Pyrrole, 2-[1-[(trimethylsilyl)oxy]ethenyl]-

HRID 985620Notes

Reaction equation

HRID 985620 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:8])[CH3:7].CCN(CC)CC.FC(F)(F)S(O[Si:22]([CH3:25])([CH3:24])[CH3:23])(=O)=O>C(Cl)Cl.C(OCC)(=O)C>[CH3:23][Si:22]([CH3:25])([CH3:24])[O:8][C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[CH2:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 140792-AcetylpyrroleHCID 65367Trimethylsilyl triflate

Product 1

HCID 225072421H-Pyrrole, 2-[1-[(trimethylsilyl)oxy]ethenyl]-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1H-pyrrol-2-yl)-ethanone (2.67 mmol, 0.29 g) in CH2Cl2 (10 ml) and Et3N (13.3 mmol, 1.90 ml) was cooled to 0° C. and treated with trimethylsilyl trifluoromethanesulfonate (5.34 mmol, 1.00 ml). The solution was held at 0° C. for 30 minutes, then diluted with ethyl acetate (75 ml) and washed with saturated aqueous sodium bicarbonate (2×20 ml) then brine (30 ml). The solution was concentrated under reduced pressure to provide crude 2-[1-(trimethyl-silanyloxy)-vinyl]-1H-pyrrole. 1H NMR (CDCl3) δ 6.77 (1H, dd, J=2.7, 1.6), 6.34 (1H, dd, J=3.2, 1.6), 6.15 (1H, t, J=2.8), 4.56 (1H, d, J=1.0), 4.31 (1H, d, J=1.0), 0.45 (9H, s), 0.25 (9H, s).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (2×20 ml)
  2. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-40fba7ac1bc54bd09e80d9fd0ea4b842
Source dataset
uspto-grants-2005_03
Patent number
US06872745B2

Reaction notes

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