Water → HCID 84733342, compound

HRID 709713Notes

Reaction equation

HRID 709713 reaction equation
[OH:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][CH:6]1C(=O)OC(C)(C)[O:8][C:7]1=[O:15].O.C(OCC)(=O)C>CN(C=O)C>[OH:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([CH2:5][CH2:6][C:7]([OH:15])=[O:8])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 117760198HCID 117760198, compound

Product 1

HCID 84733342HCID 84733342, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(3-hydroxy-2-methoxybenzyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (100 mg) in DMF (10 mL) was added water (1.0 mL), and the mixture was stirred at 90° C. for 15 hr. The reaction mixture was cooled to room temperature, and ethyl acetate was added. The mixture was washed with 1N hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (50 mg) as a yellow oil. This compound was used for the next step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe mixture was washed with 1N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d60f2f9830dd4a7cbb5976d85d994584
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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