methyl (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-yl]-2-propenoate → (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenol

HRID 2050575Notes

Reaction equation

HRID 2050575 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:26]([CH3:28])[CH3:27])[N:11](/[CH:20]=[CH:21]/[C:22](OC)=[O:23])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH:26]([CH3:28])[CH3:27])[N:11](/[CH:20]=[CH:21]/[CH2:22][OH:23])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 14849778methyl (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-yl]-2-propenoateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 14849782(E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenolYield 81.3%

Procedure

From methyl (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-yl]-2-propenoate (1.150 g) and diisobutylaluminium hydride (1M in dichloromethane, 6.62 ml) by the process as described for the preparation of Intermediate (8 a) to afford a white solid which was purified by FCC eluting with System A (2:3) to afford the title compound (0.866 g) as a white solid, λmax (EtOH) 255.2 (12,050) and 243.2 (inf) nm (ε10,915).

Workup

  1. customto afford a white solid which
  2. customwas purified by FCC
  3. washeluting with System A (2:3)

Sources & evidence

ORD record
ord-3417a2e1f5104094a8cf55cdd29e683d
Source dataset
uspto-grants-1991_05
Patent number
US05013749

Reaction notes

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