Aluminium lithium hydride → HCID 57742061, compound

HRID 1362441Notes

Reaction equation

HRID 1362441 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-10647b3c8995492594257cba1606ce11
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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