Potassium Hydroxide → HCID 19002087, compound

HRID 2259998Notes

Reaction equation

HRID 2259998 reaction equation
[CH3:1][C:2]1[C:3](/[C:16](/[CH3:28])=[CH:17]/[C:18]2[NH:19][C:20]([C:23]([O:25]CC)=[O:24])=[CH:21][N:22]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[OH-].[K+]>C(O)C>[CH3:1][C:2]1[C:3](/[C:16](/[CH3:28])=[CH:17]/[C:18]2[NH:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][N:22]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15341373HCID 15341373, compound2×

Product 1

HCID 19002087HCID 19002087, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl (E)-2-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalen-2-yl)propen-1-yl]-5imidazolecarboxylate (Compound 5, 0.043 g, 0.153 mmol) was dissolved in ethanol (2 mL) and treated with 2N aqueous KOH (0.5 mL). The solution was stirred for 20 hours at 50° C. and concentrated under vacuum. The residue was treated with ether (10 mL) and water (1 mL) and neutralized with saturated aqueous NH4Cl. The layers were separated and the aqueous layer extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was passed through a small plug of silica gel (methanol) to give the title compound as a pale yellow powder (40 mg, 80%).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue was treated with ether (10 mL) and water (1 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ac6d186d814471fa9826a143e243216
Source dataset
uspto-grants-1995_12
Patent number
US05475113

Reaction notes

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