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

HRID 2238569

Reaction equation

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]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 8027Pyrrole

HCID 2564264,4-Diethoxybut-1-ene

Product 1

HCID 132917624-(Prop-2-en-1-yl)benzaldehydeYield 456.9%

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-7eca058c50b2450abb7f4c95d689656b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718794B2

Linked notes

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