Diisobutylaluminumhydride → HCID 22493865, compound

HRID 1816425Notes

Reaction equation

HRID 1816425 reaction equation
[CH3:1][C:2]1([CH3:23])[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[C:5]([CH3:22])([CH3:21])[CH2:4][CH2:3]1)[O:13][C:12](=[O:16])[CH:11]=[C:10]3[C:17]([F:20])([F:19])[F:18].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[CH3:1][C:2]1([CH3:23])[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][C:6]=2[C:5]([CH3:22])([CH3:21])[CH2:4][CH2:3]1)[O:13][CH:12]([OH:16])[CH:11]=[C:10]3[C:17]([F:20])([F:18])[F:19]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 22493863HCID 22493863, compound2×

Product 1

HCID 22493865HCID 22493865, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 6,6,9,9-tetramethyl-4-trifluoromethyl-6,7,8,9-tetrahydro-benzo[g]chromen-2-one (Intermediate 3, 348 mg, 1.07 mmol) in CH2Cl2 (5 mL) at −78° C. was added di-iso-butyl aluminum hydride (DIBAL-H, 1.40 mL, 1.0 M in CH2Cl2) over 10 min. After stirring at −78° C. for 3 h, the reaction was quenched with aqueous NH4Cl, followed by 1M HCl, and the aqueous layer was extracted with Et2O (×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (10% EtOAc-hexane) to give the title compound as a clear oil (346 mg, 99%) that was used directly in the next reaction.

Workup

  1. customthe reaction was quenched with aqueous NH4Cl
  2. extractionthe aqueous layer was extracted with Et2O (×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (10% EtOAc-hexane)

Sources & evidence

ORD record
ord-b4e2c7e0c1834195b5cb2b08c0b81546
Source dataset
uspto-grants-2005_04
Patent number
US06884820B2

Reaction notes

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