Aluminium lithium hydride → (7-ethyl-3-methyl-1H-indol-2-yl)methanol

HRID 1362444Notes

Reaction equation

HRID 1362444 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](OCC)=[O:13])=[C:8]2[CH3:17])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([CH2:12][OH:13])=[C:8]2[CH3:17])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59277626ethyl 7-ethyl-3-methyl-1H-indole-2-carboxylate

Product 1

HCID 59277628(7-ethyl-3-methyl-1H-indol-2-yl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 7-ethyl-3-methyl-1H-indole-2-carboxylate (2.2 g, 9.5 mmol) in THF (50 mL) was added to an ice cooled solution of 1M LAH in THF (19 mL, 19.0 mmol) and stirred overnight. The reaction was quenched with ethyl acetate and sodium hydroxide, filtered through celite and evaporated to afford the title compound (1.6 g, 100%). 1H NMR (400 MHz, CDCl3) δ 8.45 (s, 1H), 7.39 (d, J=6.5 Hz, 1H), 7.04 (m, 2H), 4.80 (s, 2H), 2.83 (q, J=4.8 Hz, 2H), 2.28 (s, 3H), 1.34 (t, J=4.4 Hz, 3H)

Workup

  1. customThe reaction was quenched with ethyl acetate and sodium hydroxide
  2. filtrationfiltered through celite
  3. customevaporated

Sources & evidence

ORD record
ord-eb84e52add52413ebb05ff4ed716ac57
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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