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

HRID 2097193Notes

Reaction equation

HRID 2097193 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-d30aaa2e11c241a5bcc9184c8376cccf
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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