Trifluoroacetic acid → 5-Allyloxy-7-(4-fluoro-benzyl)-9-hydroxy-pyrrolo[3,4-g]quinoline-6,8-dione

HRID 853620ノート

反応式

HRID 853620 の反応式
[CH2:1]([O:4][C:5]1[C:14]2[C:15](=[O:27])[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:17](=[O:18])[C:13]=2[C:12]([O:28]COC)=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH:2]=[CH2:3].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:4][C:5]1[C:14]2[C:15](=[O:27])[N:16]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:17](=[O:18])[C:13]=2[C:12]([OH:28])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2)[CH:2]=[CH2:3]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 589289585-Allyloxy-7-(4-fluoro-benzyl)-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione

生成物 1

HCID 104747705-Allyloxy-7-(4-fluoro-benzyl)-9-hydroxy-pyrrolo[3,4-g]quinoline-6,8-dione収率 44%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5-Allyloxy-7-(4-fluoro-benzyl)-9-methoxymethoxy-pyrrolo[3,4-g]quinoline-6,8-dione 10 was dissolved in 1 mL dichloromethane. Ten equivalents of trifluoroacetic acid was added and the mixture was stirred at room temperature. After one hour another 10 equivalents of trifluoroacetic acid was added. The mixture was then stirred overnight, concentrated in vacuo, and azeotroped with toluene (2×), to give crude 11 which was triturated with 2 mL of 1:1 diethylether/hexane two times to give allyl ether 11 (0.0025 g, 0.0066 mmol, 44%). 1H NMR (CDCl3) δ 9.0 (s, 1H), 8.7 (d, 1H), 7.7 (m, 1H), 7.5 (m, 2H), 7.0 (t, 2H), 6.1 (m, 1H), 5.4 (d, 1H), 5.3 (d, 1H), 5.1 (d, 2H), 4.8 (s, 2H). MS: 379 (M+1).

後処理

  1. stirringThe mixture was then stirred overnight
  2. concentrationconcentrated in vacuo
  3. customazeotroped with toluene (2×)
  4. customto give crude 11 which
  5. customwas triturated with 2 mL of 1:1 diethylether/hexane two times

出典と根拠

ORDレコード
ord-d64fa2e0a1bc47a1a3fee72a0bc884ed
出典データセット
uspto-grants-2007_08
特許番号
US07253180B2

反応ノート

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