Aluminium lithium hydride → HCID 43825164, compound

HRID 2233426Notes

Reaction equation

HRID 2233426 reaction equation
CO[N:3]=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[F:12][C:8]1[CH:7]=[C:6]([CH2:5][CH:4]([NH2:3])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=2)[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86616525HCID 86616525, compound

Product 1

HCID 43825164HCID 43825164, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-fluoro-phenyl)-1-(3-trifluoromethyl-phenyl)-ethanone O-methyl-oxime (1.00 g, 3.20 mmol) in Et2O at 0° C. was added LAH (1.0 M in THF, 3.20 mL, 3.20 mmol). The reaction mixture was stirred for a few minutes, and then refluxed for 30 hours. The resulting mixture was cooled to 0° C. and quenched with a few drops of H2O. The mixture was filtered through a pad of celite, concentrated and purified by column chromatography using hexane:EtOAc (1:1) as eluant to give 470 mg of the desired title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 1.47-1.62 (m, 2 H), 2.84-2.93 (m, 1 H), 2.98-3.07 (m, 1 H), 4.28-4.35 (m, 1 H), 6.99-7.11 (m, 3 H), 7.16-7.27 (m, 1 H), 7.39-7.46 (m, 1 H), 7.52 (t, J=7.62 Hz, 2 H), 7.61 (s, 1H).

Workup

  1. temperaturerefluxed for 30 hours
  2. customquenched with a few drops of H2O
  3. filtrationThe mixture was filtered through a pad of celite,
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-2dda32907a4f49b49cefb00e76737c7c
Source dataset
uspto-grants-2010_05
Patent number
US07709507B2

Reaction notes

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