Diisobutylaluminum hydride → HCID 66727644, compound

HRID 1361218Notes

Reaction equation

HRID 1361218 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-480fd23a7f15466e89fa074529d4c5d8
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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