Aluminium lithium hydride → HCID 58303839, compound

HRID 1404103Notes

Reaction equation

HRID 1404103 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15](Br)=[C:14]2[C:10]=1[C:11]([C:20](=O)[C:21](OC)=[O:22])=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH2:20][CH2:21][OH:22])=[CH:12][NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58303890HCID 58303890, compound

Product 1

HCID 58303839HCID 58303839, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 17-2 (1.98 g, 4.874 mmol) in dry 1,4-dioxane (80 mL) was added dropwise to a slurry of LiAlH4 (1.85 g, 48.74 mmol) in dry 1,4-dioxane (40 mL) at reflux. The mixture was held at reflux for 1 h. The mixture was then cooled, quenched with 2 mL H2O, 2 mL NaOH (15%) solution, and 6 mL H2O. After stirring for 20 min, the mixture was filtered and the filtrate was concentrated. The resulting residue was purified by column chromatography on silica gel with hexanes/ethyl acetate (1:0 to 1:1) as eluent to afford 17-3 as a colorless oil in 56% yield (1.0 g). 1H NMR (300 MHz, CDCl3) δ (ppm) 7.97 (br, 1H), 7.47-7.50 (m, 2H), 7.34-7.43 (m, 3H), 6.96-6.98 (m, 3H), 5.27 (d, J=1.1 Hz, 2H), 3.74 (dt, J=6.3, 6.0 Hz, 2H), 2.96 (t, J=6.3 Hz, 2H), 1.47 (t, J=6.3 Hz, 1H). APCI [M+1]: 286.1

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was then cooled
  4. customquenched with 2 mL H2O, 2 mL NaOH (15%) solution, and 6 mL H2O
  5. filtrationthe mixture was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe resulting residue was purified by column chromatography on silica gel with hexanes/ethyl acetate (1:0 to 1:1) as eluent

Sources & evidence

ORD record
ord-883aca98123948ad8f32346f0ca0a82b
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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