Methanol → HCID 66739221, compound

HRID 1641588Notes

Reaction equation

HRID 1641588 reaction equation
FC(F)(F)S(O[CH2:7]/[CH:8]=[C:9]1/[CH:10]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[O:11][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:14]/1)(=O)=O.[O:32]1CCOCC1.CO.[OH-].[Na+]>[Cl-].[Na+].O.C(OC(=O)C)C>[N+:27]([C:24]1[CH:23]=[CH:22][C:21]([C@H:10]2[C@@H:9]([CH:8]([OH:32])[CH3:7])[CH2:14][CH2:13][C@@H:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:11]2)=[CH:26][CH:25]=1)([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86633531HCID 86633531, compound

Product 1

HCID 66739221HCID 66739221, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of (E)-(2-(4-nitrophenyl)-6-phenyl-dihydro-2H-pyran-3(4H)-ylidene)ethyl trifluoromethanesulfonate (0.3 mmol) in a mixture of 2:1 1,4-dioxane:methanol was treated with an aqueous NaOH solution (1%, 4 mL) at room temperature for 3 hours with stirring. Following completion of the reaction, brine was added to the reaction solution which was then diluted with ethylacetate. The organic layer thus formed was washed with water, dried over Na2SO4, filtered and concentrated. The purification of the concentrate afforded the title compound (Yield 75%).

Workup

  1. additionwas added to the reaction solution which
  2. customThe organic layer thus formed
  3. washwas washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe purification of the concentrate

Sources & evidence

ORD record
ord-ad574074926c46f99ce1b451c0b70d80
Source dataset
uspto-grants-2012_02
Patent number
US08115019B2

Reaction notes

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