Diisobutylaluminum hydride → HCID 44430246, compound

HRID 230413Notes

Reaction equation

HRID 230413 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[C:10]2[CH:11]=[C:12]([Cl:16])[C:13]([Cl:15])=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:17][C:18]([F:21])([F:20])[F:19])C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Cl:15][C:13]1[C:12]([Cl:16])=[CH:11][C:10]2[N:6]([CH2:5][CH2:4][OH:3])[C:7]([CH2:17][C:18]([F:19])([F:20])[F:21])=[N:8][C:9]=2[CH:14]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 59682295HCID 59682295, compound

Product 1

HCID 44430246HCID 44430246, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To [5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-benzimidazol-1-yl]-acetic acid ethyl ester (915 mg) in toluene (20 mL) at −78° C. was added DiBAl—H (3.43 mls of 1.5 M in toluene). The resulting mixture was stirred for 1 hour. The reaction mixture was quenched with Rochelle's salt (aq), extracted with EtOAc, and dried over Na2SO4. The extracts were concentrated to a toluene solution and ethanol (10 mL) was added. To the resulting solution was added NaBH4 (533 mg). The resulting mixture was stirred for 5 hour. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (15%-60% EtOAc/hexanes) to yield the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with Rochelle's salt (aq)
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. concentrationThe extracts were concentrated to a toluene solution and ethanol (10 mL)
  5. additionwas added
  6. additionTo the resulting solution was added NaBH4 (533 mg)
  7. stirringThe resulting mixture was stirred for 5 hour
  8. customThe reaction mixture was quenched with water
  9. extractionextracted with EtOAc
  10. dry with materialdried over Na2SO4
  11. customThe crude product was purified by silica gel chromatography (15%-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-de3b75d8b9134974b886a86569fb6982
Source dataset
uspto-grants-2009_07
Patent number
US07566733B2

Reaction notes

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