Toluene → HCID 59321562, compound

HRID 2423491Notes

Reaction equation

HRID 2423491 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:12]([C:13](OC)=[O:14])=[C:11]([CH:17]([CH3:19])[CH3:18])[O:10][N:9]=2)=[C:6]([Cl:20])[CH:5]=[CH:4][N:3]=1.[H-].C([Al+]C(C)C)(C)C.C1(C)C=CC=CC=1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH:17]([CH3:18])[CH3:19])[O:10][N:9]=2)=[C:6]([Cl:20])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 9357Potassium Sodium TartrateHCID 21896610Diisopropylaluminium hydrideHCID 59321564HCID 59321564, compound

Product 1

HCID 59321562HCID 59321562, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolecarboxylate (1.32 g, 4.2 mmol) in THF (11.7 mL) was stirred at a 0° C. as a 1.5 M solution of diisopropylaluminum hydride in toluene (9 mL, 13.4 mmol) was added; the solution was allowed to warm to room temperature and stirred overnight. A 10% aqueous solution of Rochelle's salt was added and the solution was then allowed to stir for three hours. The layers were separated and the organic layer was washed with brine. The organic layer was dried with MgSO4, filtered and concentrated. The residue was purified by chromatography (silica gel, hexane to ethyl acetate gradient elution) to yield [3-(2,4-dichloro-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methanol (1.20 g, 94% 0.2 ethyl acetate). 1H NMR (400 MHz, DMSO-d6): δ 8.52 (d, J=5 Hz, 1H), 7.78 (d, J=5 Hz, 1H), 4.94 (t, J=5 Hz, 1H), 4.20 (d, J=5 Hz, 2H), 3.34 (septet, J=7 Hz, overlapping water), 1.29 (d, J=7 Hz, 6H).

Workup

  1. additionwas added
  2. stirringto stir for three hours
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (silica gel, hexane to ethyl acetate gradient elution)

Sources & evidence

ORD record
ord-d42e375a885c47e9996fbcfd46c12cc7
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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