Tetrahydrofuran → (1H-indol-7-yl)methanol

HRID 1817985Notes

Reaction equation

HRID 1817985 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10](OC)=[O:11])[CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:20]1COC[CH2:21]1>>[CH2:20]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:21].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:10][OH:11])[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 676694Methyl indole-7-carboxylateHCID 21226445Aluminium lithium hydride

Product 2

HCID 2773460(1H-indol-7-yl)methanolYield 98%HCID 38016182-ethyl-1H-indole

Procedure

Indole-7 carboxyldehyde (I-1). Ethyl Indole-7 m carboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. Vol IIV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in 250 ml of anhydrous THF was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2 h. After cooling to room temperature, the excess hydride was quenched by addition of water (12 mL), 15% NaOH (12 mL) and water (26 mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (1H-indol-7-yl)-methanol (10.7 g, 98%). 1HNMR (CDCl3). To a solution of the alcohol, (1H-indol-7-yl)-methanol (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85%, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72 h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield 1H-indole-7-carbaldehyde, I-1 (6.55 g, 83%). 1HNMR (CDCl3).

Workup

  1. customin portions, and reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 2 h
  4. customthe excess hydride was quenched by addition of water (12 mL), 15% NaOH (12 mL) and water (26 mL)
  5. customThe solids were removed by filtration through a pad of Celite and filtrate
  6. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-01a3cb7395ca42319f1b2b926dff0bd4
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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