Diisobutylaluminum hydride → HCID 18788498, compound

HRID 1940128Notes

Reaction equation

HRID 1940128 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[F:27])[O:5][C:6]1[C:7](=[O:23])[O:8][C:9]([CH3:22])([CH3:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:21][C:9]1([CH3:22])[O:8][CH:7]([OH:23])[C:6]([O:5][C:4]2[CH:24]=[CH:25][C:26]([F:27])=[C:2]([F:1])[CH:3]=2)=[C:10]1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 99086243-(3,4-Difluorophenoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

Product 1

HCID 18788498HCID 18788498, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3-(3,4-difluorophenoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one (500 mg, 1.27 mmol) in 10 mL of THF was added DIBAL (1.5M in toluene, 2.8 mL, 4.2 mmol). Warmed to r.t. and stirred 30 min. The reaction was quenched with acetone, followed by 0.5M sodium potassium tartrate and stirred overnight. The mixture was extracted with EtOAc, washed with brine, dried over MgSO4, filtered and concentrated. Crystalization from CH2Cl2 /toluene provided 350 mg of the title compound.

Workup

  1. customThe reaction was quenched with acetone
  2. stirringstirred overnight
  3. extractionThe mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrystalization from CH2Cl2 /toluene

Sources & evidence

ORD record
ord-6debdad55722474e9c015add33812045
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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