Diisobutylaluminumhydride → HCID 178463126, compound

HRID 1738359Notes

Reaction equation

HRID 1738359 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:28])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([N:20]3[CH2:25][CH2:24][O:23][C:22](=[O:26])[CH2:21]3)[C:11]=2[Cl:27])[CH:5]=[N:4]1)[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:28])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([N:20]3[CH2:25][CH2:24][O:23][CH:22]([OH:26])[CH2:21]3)[C:11]=2[Cl:27])[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 178463125HCID 178463125, compound

Product 1

HCID 178463126HCID 178463126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.38 g (3.22 mmol) of 1-ethyl-4-(2-chloro-3-(morpholin-2-on-4-yl)-4-methylsulfonylbenzoyl)-5-hydroxypyrazole in 200 mL of dichloromethane was cooled to -78° C. and treated dropwise with stirring with 7.0 ml, (7.0 mmol) of a 1M solution of diisobutylaluminum hydride in dichloromethane. After 15 min, the reaction was quenched with 5 mL of methanol and 100 mL of 1N aqueous hydrochloric acid and was then allowed to warm to room temperature with vigorous stirring for 30 min. The layers were separated and the aqueous layer was washed with dichloromethane. The organic layers were combined and concentrated by evaporation under reduced pressure. The residue was dissolved in a mixture of acetonitrile and 1N aqueous hydrochloric acid. The mixture was stirred for a few minutes and was then diluted with dichloromethane. The solution obtained was washed with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure. The resulting solid residue was extracted with ethanol and dried to obtain 1.20 g (87 percent of theory) of the title compound as a tan powder melting at 209-210° C.

Workup

  1. additiontreated dropwise
  2. customthe reaction was quenched with 5 mL of methanol and 100 mL of 1N aqueous hydrochloric acid
  3. customThe layers were separated
  4. washthe aqueous layer was washed with dichloromethane
  5. concentrationconcentrated by evaporation under reduced pressure
  6. dissolutionThe residue was dissolved in a mixture of acetonitrile and 1N aqueous hydrochloric acid
  7. stirringThe mixture was stirred for a few minutes
  8. additionwas then diluted with dichloromethane
  9. customThe solution obtained
  10. washwas washed with water
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated by evaporation under reduced pressure
  13. extractionThe resulting solid residue was extracted with ethanol
  14. customdried

Sources & evidence

ORD record
ord-e9baedddf6c84608aa4b556c16c70b13
Source dataset
uspto-grants-1999_10
Patent number
US05962690

Reaction notes

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