N,N-Dimethylformamide--water (1/1) → HCID 59590857, compound

HRID 2098976Notes

Reaction equation

HRID 2098976 reaction equation
[CH2:1]([C:3]1([CH:14]2C(=O)OC(C)(C)[O:16][C:15]2=[O:23])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].CN(C=O)C.O>CCOC(C)=O>[CH2:1]([C:3]1([CH2:14][C:15]([OH:23])=[O:16])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 21962138N,N-Dimethylformamide--water (1/1)HCID 59590904HCID 59590904, compound

Product 1

HCID 59590857HCID 59590857, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A 100 mL round bottom flask was charged with 42.1 (0.30 g, 0.94 mmol) and 10:1 DMF/water (5 mL). The solution was stirred overnight at 90° C., cooled to room temperature, and diluted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by silica gel flash chromatography (0-30% EtOAc/hexanes) to afford 42.2 (0.204 g, 92% yield) as a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e0d0615222944d139b0379b3605c7940
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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