Trifluoroacetic acid → 4-(Prop-2-en-1-yl)benzaldehyde

HRID 2238569

Reaktionsgleichung

Reaktionsgleichung von HRID 2238569
C(O[CH:4]([O:8]CC)[CH2:5][CH:6]=[CH2:7])C.N1[CH:15]=[CH:14][CH:13]=[CH:12]1.[C:16](O)([C:18](F)(F)F)=O>>[CH2:14]([C:15]1[CH:7]=[CH:6][C:5]([CH:4]=[O:8])=[CH:18][CH:16]=1)[CH:13]=[CH2:12]

Komponenten

4

Edukt 3

HCID 6422Trifluoroacetic acidHCID 8027PyrroleHCID 2564264,4-Diethoxybut-1-ene

Produkt 1

HCID 132917624-(Prop-2-en-1-yl)benzaldehydeAusbeute 456,9 %

Versuchsvorschrift

5-Allyldipyrromethane (24). Following a standard procedure,40,41 a solution of 3-butenal diethylacetal (4.00 g, 27.7 mmol) in pyrrole (194 mL, 2.77 mol) at room temperature under argon was treated with TFA (467 μL, 2.77 mmol) for 10 min. TEA (221 μL, 2.77 mmol) was added. The mixture was concentrated under high vacuum. The residue was chromatographed [silica, hexanes/ethyl acetate (4:1)] to afford a pale orange oil (1.85 g, 36%): 1H NMR δ 2.86 (t, J=8.0 Hz, 2H), 4.11 (t, J=8.0 Hz, 1H), 5.02-5.12 (m, 2H), 5.83 (m, 1H), 6.08 (s, 2H), 6.15 (m, 2H), 6.65 (m, 2H), 7.83 (br s, 2H); 13C NMR δ 37.3, 38.7, 105.6, 107.6, 116.3, 117.1, 132.8, 136.2; FABMS obsd 187.1230, calcd 187.1235 [(M+H)+], (M=C12H14N2).

Aufarbeitung

  1. customat room temperature
  2. concentrationThe mixture was concentrated under high vacuum
  3. customThe residue was chromatographed [silica, hexanes/ethyl acetate (4:1)]

Quellen und Nachweise

ORD-Eintrag
ord-7eca058c50b2450abb7f4c95d689656b
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718794B2

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