Sodium Hydroxide → 2384666-57-1

HRID 920805Notes

Reaction equation

HRID 920805 reaction equation
[F:1][C:2]1([F:14])[C:4]2([CH2:7][C:6]([CH3:13])([C:8]([O:10]CC)=[O:9])[CH2:5]2)[CH2:3]1.[OH-].[Na+]>C1COCC1.O>[F:1][C:2]1([F:14])[C:4]2([CH2:5][C:6]([CH3:13])([C:8]([OH:10])=[O:9])[CH2:7]2)[CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118062215HCID 118062215, compound

Product 1

HCID 1180618232384666-57-1

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 326A (0.5 g, 2.448 mmol) in THF (10 mL) and water (5 mL) was added NaOH (0.245 g, 6.12 mmol) and the reaction mixture was stirred at RT for 16 h. The volatiles were removed from the reaction mixture and the pH of the resulting residue was adjusted to ˜3 using a 1.0 N aq. solution of HCl. The aqueous layer was extracted with EtOAc (3×10 mL) The combined organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated to afford Intermediate 326B (0.35 g, 81%, a mixture of cis and trans isomers) as a yellow liquid used directly in the next step without purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.39 (br. s., 1H), 2.55-2.63 (m, 2H), 1.89-2.02 (m, 2H), 1.34-1.45 (m, 3H), 1.14-1.23 (m, 2H).

Workup

  1. customThe volatiles were removed from the reaction mixture
  2. extractionThe aqueous layer was extracted with EtOAc (3×10 mL) The combined organic layer
  3. washwas washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4dadd67dd5eb4ea58d6e7ae358e9249d
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

Loading…