Potassium Hydroxide → HCID 9863484, compound

HRID 1379796Notes

Reaction equation

HRID 1379796 reaction equation
[CH3:1][C:2]1[C:3]([S:16][C:17]2[N:27]=[CH:26][CH:25]=[CH:24][C:18]=2[C:19]([O:21]CC)=[O:20])=[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]([S:16][C:17]2[N:27]=[CH:26][CH:25]=[CH:24][C:18]=2[C:19]([OH:21])=[O:20])=[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 22908106HCID 22908106, compound2×

Product 1

HCID 9863484HCID 9863484, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2 - (5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthylthio)nicotinate (Compound 12, 300 mg, 0.78mmol) and ethanol (8 mL) was added 2N KOH (2 mL) and the resulting solution stirred at 50° C. for 34 h. The solution was concentrated in vacuo, water added, and the mixture was acidified with 10% aqueous HCl. The product was extracted with methylene chloride (3×) and the combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The solid residue was recrystalized from acetonitrile/methanol (4:1) to give the title compound (233 mg, 84%) as light yellow crystals:

Workup

  1. concentrationThe solution was concentrated in vacuo, water
  2. additionadded
  3. extractionThe product was extracted with methylene chloride (3×)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe solid residue was recrystalized from acetonitrile/methanol (4:1)

Sources & evidence

ORD record
ord-4506b59de748459d9a2f16966f51837b
Source dataset
uspto-grants-1997_09
Patent number
US05672710

Reaction notes

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