Ethyl Acetate → HCID 68492350, compound

HRID 498984Notes

Reaction equation

HRID 498984 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](CC(CC=C)C#N)[CH:6]=[CH:5]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[CH2:28][CH3:29])(=O)C>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:3][CH:4]([CH2:5][CH:28]=[CH2:29])[CH2:8][NH2:7])=[CH:5]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 57450600HCID 57450600, compound

Product 1

HCID 68492350HCID 68492350, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 51 (8.82 g, 39.3 mmol) in THF (400 mL) at 0° C. was added LiAlH4 (4.77 g, 118 mmol). The mixture was stirred at room temperature overnight, then cooled to −78° C. and ethyl acetate (60 mL) was added followed by 10% NaOHaq (15 mL). The reaction was quenched by the addition of moister Na2SO4, filtered through celite, washed with EtOAc (3×100 mL) and MeOH (3×150 mL). Evaporation provided a residue, which was purified by silica gel flash chromatography to provide 52 as colorless oil. (3.52 g, 39% yield). H NMR (d6-DMSO) δ 7.34-7.27 (m, 3H), 6.93 (d, 1H, J=1.5 Hz & 8.3 Hz), 6.31 (d, 1H, J=3.0 Hz), 5.78 (m, 1H), 5.06-4.99 (m, 2H), 4.16 (dd, 1H, J=7.0 Hz & 14.2 Hz), 4.00 (dd, 1H, J=6.5 Hz & 14.2 Hz), 2.42 (t, 2H, J=4.5 Hz), 2.36 (s, 3H), 2.05 (m, 1 H), 1.98-1.90 (m, 2H). FABMS (+Ve) m/z 229 [MH+].

Workup

  1. temperaturecooled to −78° C.
  2. customThe reaction was quenched by the addition of moister Na2SO4
  3. filtrationfiltered through celite
  4. washwashed with EtOAc (3×100 mL) and MeOH (3×150 mL)
  5. customEvaporation
  6. customprovided a residue, which
  7. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-e22dc20e83b2484da2b1bbdcb0ff48c1
Source dataset
uspto-grants-2010_08
Patent number
US07767645B2

Reaction notes

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