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

HRID 50992노트

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HRID 50992 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3039d00c888c4f88a1e473c279218273
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713471B1

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