Aluminium lithium hydride → HCID 57742061, compound

HRID 2097190Notes

Reaction equation

HRID 2097190 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:15](OCC)=[O:16].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([C:11]([F:14])([F:12])[F:13])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:15][OH:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57742098HCID 57742098, compound

Product 1

HCID 57742061HCID 57742061, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 3-methyl-7-(trifluoromethyl)-1H-indole-2-carboxylate (2.2 g, 8.1 mmol) in THF (50 mL) was added to an ice cooled solution of 1M LAH in THF (16.2 mL, 16.2 mmol) and stirred overnight. The reaction was quenched with ethyl acetate and sodium hydroxide, filtered through celite and evaporated to afford the title compound (1.03 g, 57%). 1H NMR (400 MHz, CDCl3) δ 8.74 (s, 1H), 7.66 (d, J=7.9 Hz, 1H), 7.40 (d, J=7.3 Hz, 1H), 7.12 (t, J=4.7 Hz, 1H), 4.81 (s, 2H), 2.26 (s, 3H)

Workup

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

Sources & evidence

ORD record
ord-3e690a854e4c45d8b3b2613fc3124989
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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