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

HRID 2225037

Reaktionsgleichung

Reaktionsgleichung von HRID 2225037
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-fe28b1bbea2a4726be29ea90d3fa0e21
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378520B2

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