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

HRID 2225037

反応式

HRID 2225037 の反応式
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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-fe28b1bbea2a4726be29ea90d3fa0e21
出典データセット
uspto-grants-2008_05
特許番号
US07378520B2

関連ノート

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