Diisobutylaluminum hydride → 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol

HRID 468514ノート

反応式

HRID 468514 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:19])([CH3:18])[CH2:12][C:13](OCC)=[O:14])[NH:8]2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([CH3:19])([CH3:18])[CH2:12][CH2:13][OH:14])[NH:8]2)=[CH:4][C:3]=1[N+:20]([O-:22])=[O:21]

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 59129505ethyl 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutanoate

生成物 1

HCID 591293673-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol収率 22.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of ethyl 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutanoate (34 g, 0.11 mol) in dry CH2Cl2 (400 mL) was added drop-wise DIBAL-H (283.4 mL, 0.27 mol) over 2 hours at −78° C. The reaction mixture was stirred for 10 hours at −78° C. and then quenched by adding water (200 mL). The precipitate was filtered off and washed with methanol. The filtrate was extracted with CH2Cl2 (200 mL×3), the combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 50:1) to give 3-(6-fluoro-5-nitro-1H-indol-2-yl)-3-methylbutan-1-ol (6.6 g, 22%). 1H NMR (400 MHz, CDCl3) δ 9.35 (brs, 1H), 8.30 (d, J=7.6 Hz, 1H), 7.11 (d, J=12.0 Hz, 1H), 6.35 (d, J=1.2 Hz, 1H), 3.74 (t, J=6.4 Hz, 2H), 1.9 (t, J=6.4 Hz, 2H), 1.4 (s, 6H).

後処理

  1. customquenched
  2. additionby adding water (200 mL)
  3. filtrationThe precipitate was filtered off
  4. washwashed with methanol
  5. extractionThe filtrate was extracted with CH2Cl2 (200 mL×3)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 50:1)

出典と根拠

ORDレコード
ord-3f7f28ecf0b94c40b7c7597b47642d07
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

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