Potassium Carbonate → HCID 69662645, compound

HRID 2214851Notes

Reaction equation

HRID 2214851 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1C=O.[F:14][C:15]([F:24])([F:23])/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19].[C:25]([O-])([O-])=O.[K+].[K+]>CN(C)C=O.O>[F:14][C:15]([F:23])([F:24])[C:16]1[CH2:25][O:1][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]=2[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 128192-Hydroxy-1-naphthaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Product 1

HCID 69662645HCID 69662645, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-1-naphthaldehyde (8.6 g, 0.050 mol) and ethyl 4,4,4-trifluorocrotonate (9.2 g, 0.055 mol) dissolved in anhydrous dimethylformamide (DMF) and treated with anhydrous K2CO3 (13.8 g, 0.100 mol). The solution was maintained at room temperature for 50 hours and diluted with water. The solution was extracted with ethyl acetate, and the combined extracts were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford 4.8 g of an oil. The oil was purified by HPLC, eluting with hexanes:ethyl acetate (30:1). The appropriate fractions were concentrated to afford 1.6 g (10%) of the napthopyran ester as a yellow solid.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe combined extracts were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4164c8c8cc634930a54b07cdaeeda3c1
Source dataset
uspto-grants-2006_09
Patent number
US07109211B2

Reaction notes

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