Diisobutylaluminum hydride → HCID 18788499, compound

HRID 1940131Notes

Reaction equation

HRID 1940131 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:24])[CH2:11][CH2:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]([OH:24])[CH2:11][CH2:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 9798392212126-32-4

Product 1

HCID 18788499HCID 18788499, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a -78° C. solution of 2-(3,5-Difluorophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one (98 mg, 0.28 mmol) in THF (5 mL) was added DIBAL (1.5M toluene solution, 0.4 mL, 0.6 mmol). The solution was warmed to 0° C. and stirred 15 min, then cooled to -78° C. and quenched with 0.5 mL acetone. The solution was warmed and poured into 1M sodium potassium tartrate. The mixture was extracted with EtOAc, washed with brine, and dried over MgSO4. Crystallization from ether/hexanes provided the title compound (90 mg).

Workup

  1. temperaturecooled to -78° C.
  2. customquenched with 0.5 mL acetone
  3. temperatureThe solution was warmed
  4. additionpoured into 1M sodium potassium tartrate
  5. extractionThe mixture was extracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. customCrystallization from ether/hexanes

Sources & evidence

ORD record
ord-1c56f4c08ce14a6aa74d405a261b9afa
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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