Sodium Hydroxide → HCID 59541829, compound

HRID 2388337Notes

Reaction equation

HRID 2388337 reaction equation
[I-].[O:2]1[C:6]2([CH2:11][CH2:10][C:9]([C:12]3[CH:17]=[CH:16][N+:15]([CH3:18])=[CH:14][CH:13]=3)=[CH:8][CH2:7]2)[O:5][CH2:4][CH2:3]1.[OH-:19].[Na+]>C1COCC1>[O:2]1[C:6]2([CH2:11][CH2:10][C:9]([C:12]3[CH:13]=[CH:14][N:15]([CH3:18])[C:16](=[O:19])[CH:17]=3)=[CH:8][CH2:7]2)[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66750436HCID 66750436, compound

Product 1

HCID 59541829HCID 59541829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-1-methyl-pyridinium iodide (as prepared in the previous step, 864 mg, 2.40 mmol) in THF (5 mL) and 1N NaOH (5 mL) was treated with K3Fe(CN)6 (Aldrich, 1.58 g, 4.80 mmol) at room temperature for 4 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow oil, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil, which
  7. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-8abce4cc55264e6fab0612c7503eb275
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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