Water → HCID 14849855, compound

HRID 892965Notes

Reaction equation

HRID 892965 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:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][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]=[CH:24][N:25]=[CH:26][CH:27]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21225700DiisobutylaluminumhydrideHCID 86745904HCID 86745904, compound

Product 1

HCID 14849855HCID 14849855, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred suspension in toluene of methyl (E)-3-[5-(4-fluorophenyl)-2-(1-methylethyl)-4-(4-pyridinyl)-1H-imidazol-1-yl]-2-propenoate, 1'-oxide, (0.22 g), at -78° under nitrogen was treated with diisobutylaluminium hydride (1.5M in toluene; 0.8 ml). The mixture was stirred at -40° for 1 h and then allowed to warm to 0° before addition of water (1 ml) and ethyl acetate (20 ml). After stirring for 0.5 h the organic layer was separated, washed with brine, dried and evaporated to dryness. The residue was purified by CC eluting with a mixture of ethyl acetate, petroleum ether (bp. 40°-60°) and methanol (5:5:2) to give the title compound (0.05 g), δ(CDCl3) 8.39(m,2H,C-2 and C-6 protons of pyridine), 6.60(d,1H,J15 Hz,NCH=CH), 5.58(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. stirringAfter stirring for 0.5 h the organic layer
  2. customwas separated
  3. washwashed with brine
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by CC
  7. washeluting with a mixture of ethyl acetate, petroleum ether (bp. 40°-60°) and methanol (5:5:2)

Sources & evidence

ORD record
ord-731bba0514674a34aa8283ffd4478a69
Source dataset
uspto-grants-1992_06
Patent number
US05120848

Reaction notes

Loading…