Water → HCID 83824584, compound

HRID 709667Notes

Reaction equation

HRID 709667 reaction equation
[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[CH:5]2C(=O)OC(C)(C)[O:7][C:6]2=[O:14])[CH2:3][CH2:2]1.O>CN(C=O)C>[CH:1]1([CH:4]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[CH2:5][C:6]([OH:14])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 962WaterHCID 117759790HCID 117759790, compound

Product 1

HCID 83824584HCID 83824584, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(cyclopropyl(4-fluoro-3-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (2.00 g) in DMF (20 mL) was added water (2.0 mL), and the mixture was stirred at 90° C. for 15 hr. The reaction mixture was allowed to cool to room temperature, and extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.10 g) as a yellow oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-21d3b66ae82140dd9eaed5997d02194f
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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