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

HRID 2225037

반응식

HRID 2225037 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-fe28b1bbea2a4726be29ea90d3fa0e21
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378520B2

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