Diisobutylaluminumhydride → HCID 14849865, compound

HRID 892966Notes

Reaction equation

HRID 892966 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[C:15](OC)=[O:16])[C:11]([CH:19]([CH3:21])[CH3:20])=[N:10][C:9]=2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12](/[CH:13]=[CH:14]/[CH2:15][OH:16])[C:11]([CH:19]([CH3:21])[CH3:20])=[N:10][C:9]=2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86745905HCID 86745905, compound

Product 1

HCID 14849865HCID 14849865, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (E)-3-[5-(4-fluorophenyl)-2-(1-methylethyl)-4-(3-pyridinyl)-1H-imidazol-1-yl]-2-propenoate, 1'-oxide (0.18 g) in dichloromethane (3 ml) at 3° under nitrogen was treated with diisobutylaluminium hydride (1.5M in toluene; 0.94 ml). The mixture was stirred at 0° for 1 h and then quenched with water (1 ml) and extracted with ethyl acetate. The extracts were washed with brine, dried and evaporated. The residue was purified by CC eluting with a mixture of ethyl acetate, petroleum ether (bp. 40°-60°) and methanol (10:10:3) to give the title compound (0.05 g), δ(CDCl3) 8.60(m,1H,C-2 proton of pyridine), 8.48(m,1H,C-6 proton of pyridine), 7.81(m,1H, C-3 proton of pyridine), 6.63(d,1H,J15 Hz,NCH=CH), 5.56(dd,1H, J15 and 6 Hz,NCH=CH), 4.18(m,2H,CH2OH), 3.17(septet,1H,J7 Hz, CH(CH3)2), 1.42(d,6H,J7 Hz,CH(CH3)2).

Workup

  1. customquenched with water (1 ml)
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by CC
  7. washeluting with a mixture of ethyl acetate, petroleum ether (bp. 40°-60°) and methanol (10:10:3)

Sources & evidence

ORD record
ord-0a25c96699f042d4a28f5377b41e2295
Source dataset
uspto-grants-1992_06
Patent number
US05120848

Reaction notes

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