Methyl 3-(1-methylindol-3-YL)propanoate → 3-(1-Methyl-1H-indol-3-yl)propan-1-ol

HRID 1764868ノート

反応式

HRID 1764868 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][C:13](OC)=[O:14])=[CH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][CH2:13][OH:14])=[CH:3]1

参加物

4

反応物 2

HCID 13679809Methyl 3-(1-methylindol-3-YL)propanoateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 227358873-(1-Methyl-1H-indol-3-yl)propan-1-ol収率 96%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a solution of methyl 3-(1-methyl-3-indolyl)propionate (300 mg, 1.38 mmol) in Et2O (3.0 mL) was added LiAlH4 at 0° C. under N2 atmosphere. The reaction mixture was stirred for 30 min at 0° C. and quenched by careful addition of H2O. EtOAc was added to the quenched reaction mixture. The organic layer was separated, washed with brine and dried over MgSO4. It was then concentrated in vacuo and chromatographed on a silica gel column by elution with EtOAc/Hexanes to give 3-(1-methyl-3-indolyl)-1-propanol (250 mg, 96%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ1.28 (t, 1H, J=6.2 Hz), 1.98 (qu, 2H, J=7.7 Hz), 2.85 (t, 2H, J=7.3 Hz), 3.70-3.78 (m, 4H), 6.86 (s, 1H), 7.10 (dt, 1H, J=1.1, 7.0 Hz), 7.22 (dt, 1H, J=1.1, 7.5 Hz), 7.29 (d, 1H, J=8.1 Hz), 7.60 (d, 1H, J=7.7 Hz) ppm.

後処理

  1. customquenched by careful addition of H2O
  2. additionEtOAc was added to the quenched reaction mixture
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationIt was then concentrated in vacuo
  7. customchromatographed on a silica gel column by elution with EtOAc/Hexanes

出典と根拠

ORDレコード
ord-316ac458b72d4cf5bab1c1ba6845173c
出典データセット
uspto-grants-2007_06
特許番号
USRE039679E1

反応ノート

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