Toluene → HCID 70044288, compound

HRID 1646125Notes

Reaction equation

HRID 1646125 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[O:18][C:19]([CH3:22])=[CH:20][CH:21]=2)/[C:12](OC)=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[O:18][C:19]([CH3:22])=[CH:20][CH:21]=2)/[CH2:12][OH:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 86746470methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(5-methyl-2-furyl)methyl-2-propenoate

Product 1

HCID 70044288HCID 70044288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(5-methyl-2-furyl)methyl-2-propenoate (Example 6, Method A) (1.5 mmol) in dry tetrahydrofuran (10 mL) held at -78° C. under argon is treated dropwise with a solution of diisobutyl aluminum hydride in toluene (3.30 mmol, 2.2 mL of 1.5M). The mixture is allowed to warm to ambient temperature and stirred an additional 17 hours. Excess reducing agent is quenched with methanol and water, dilute acetic acid and methylene dichloride are added, and the organic layer is washed with sodium bicarbonate solution, dried and concentrated to give the title compound.

Workup

  1. customheld at -78° C. under argon
  2. customis quenched with methanol and water, dilute acetic acid and methylene dichloride
  3. additionare added
  4. washthe organic layer is washed with sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ced3df609d3443e92f904ee61d7f58d
Source dataset
uspto-grants-1993_01
Patent number
US05177096

Reaction notes

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