Diisobutylaluminumhydride → HCID 59240150, compound

HRID 1673052Notes

Reaction equation

HRID 1673052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([C:13](OCC)=[O:14])[N:10]=[C:9]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:26]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[C:9]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59240183HCID 59240183, compound

Product 1

HCID 59240150HCID 59240150, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −78° C. solution of ethyl 1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazole-4-carboxylate (1.00 g, 1.94 mmol) in 10 mL dichloromethane was added diisobutylaluminum hydride (9.7 mL, 9.70 mmol). The reaction was stirred from 78° C. to room temperature for 12 h. The reaction was quenched with 5 mL MeOH, followed by 10 mL Rochelle's salt. Dilute with ethyl acetate and stir for 1 h. The organic layer was separated and the water layer was extracted with ethyl acetate 1×10 mL. The combined organic layers were washed with brine and dried with MgSO4 to afford (1-(3-chloro-3′-(methylsulfonyl)biphenyl-4-yl)-2-(2-chlorophenyl)-1H-imidazol-4-yl)methanol (770 mg, 84%) as a white solid. 1H-NMR (DMSO, 400 MHz) δ 8.21-8.20 (m, 1H), 8.10-8.07 (m, 1H), 8.05-8.04 (m, 1H), 7.95-7.92 (m, 1H), 7.80-7.77 (m, 1H), 7.74 (t, J=7.84 Hz, 1H), 7.49-7.46 (m, 2H), 7.45-7.31 (m, 4H), 5.11 (t, J=5.69 Hz, 1H), 4.50 (d, J=5.79 Hz, 2H), 3.29 (s, 3H); MS (ES) 473.3 [M+H]+ and 495.0 [M+Na]+.

Workup

  1. customThe reaction was quenched with 5 mL MeOH
  2. additionDilute with ethyl acetate
  3. stirringstir for 1 h
  4. customThe organic layer was separated
  5. extractionthe water layer was extracted with ethyl acetate 1×10 mL
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-fe0fcf3d3cbb4f519c7cc2299eae2f8c
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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