Toluene → HCID 67849149, compound

HRID 1033890Notes

Reaction equation

HRID 1033890 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:7](/[CH:10]=[CH:11]/[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]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:7](/[CH:10]=[CH:11]/[CH2:12][OH:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 10042420HCID 10042420, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 67849149HCID 67849149, 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-propenoate (Example 11, Method A) (0.5 g, 1.5 mmol) in dry tetrahydrofuran (10 mL) held at -78° C. under argon was treated dropwise with a solution of diisobutyl aluminum hydride in toluene (3.30 mmol, 2.2 mL of 1.5 M). The mixture was allowed to warm to ambient temperature and stirred an additional 17 hours. Excess reducing agent was quenched with methanol and water, dilute acetic acid and methylene chloride were added, and the organic layer was washed with sodium bicarbonate solution, dried and concentrated to 0.507 g of the title compound as an oil.

Workup

  1. customheld at -78° C. under argon
  2. customwas quenched with methanol and water, dilute acetic acid and methylene chloride
  3. additionwere added
  4. washthe organic layer was washed with sodium bicarbonate solution
  5. customdried
  6. concentrationconcentrated to 0.507 g of the title compound as an oil

Sources & evidence

ORD record
ord-5633fb660eb44ddb92676ec81bd4d7ef
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

Loading…