Diisobutylaluminum hydride → HCID 66727644, compound

HRID 1698219Notes

Reaction equation

HRID 1698219 reaction equation
[Br:1][C:2]1[CH:6]=[C:5](/[CH:7]=[N:8]/[S:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[O:4][N:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:6]=[C:5]([CH2:7][NH:8][S:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[O:10])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 87126736HCID 87126736, compound

Product 1

HCID 66727644HCID 66727644, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (−78° C.) yellow solution of 2-methyl-propane-2-sulfinic acid 1-(3-bromo-isoxazol-5-yl)-meth-(E)-ylideneamide (129 mg, 0.462 mmol) in THF (7 mL) was added a 1 M solution of DIBAH (1.2 mL, 1.2 mmol) in hexanes dropwise. After 1.5 hours, the reaction was quenched with MeOH (4 mL) and the cold bath was removed. The mixture was concentrated in vacuo and the residue was treated with 1 N aqueous NaOH (10 mL) and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 2-methyl-propane-2-sulfinic acid (3-bromo-isoxazol-5-ylmethyl)-amide which was used without further purification. MS m/z 281.35 (M), 283.32 (M+2).

Workup

  1. customthe reaction was quenched with MeOH (4 mL)
  2. customthe cold bath was removed
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was treated with 1 N aqueous NaOH (10 mL)
  5. extractionextracted with EtOAc (3×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fefc8c92c1b84a62b4557d011f722a6b
Source dataset
uspto-grants-2012_04
Patent number
US08163918B2

Reaction notes

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