Ethyl acetate hexane → 3-Isopropyl-2-(tetrahydropyran-4-yl)maleic anhydride

HRID 1774397Notes

Reaction equation

HRID 1774397 reaction equation
O[C:2]([CH:16]([CH3:18])[CH3:17])([CH:6]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[C:7]([OH:9])=[O:8])[C:3](O)=[O:4].CCCCCC.C(OCC)(=O)C>C(OC(=O)C)(=O)C>[CH:16]([C:2]1=[C:6]([CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:7]([O:9][C:3]1=[O:4])=[O:8])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 666488882-Hydroxy-2-isopropyl-3-(tetrahydropyran-4-yl)succinic acid

Product 1

HCID 597065373-Isopropyl-2-(tetrahydropyran-4-yl)maleic anhydrideYield 67%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2-Hydroxy-2-isopropyl-3-(tetrahydropyran-4-yl)succinic acid (70 mg, 0.27 mmol) was dissolved in acetic anhydride (1 mL), and the solution was left standing at 120° C. for 10 h. The acetic anhydride was evaporated under reduced pressure and the residue thus obtained was subjected to silica gel column chromatography (hexane-ethyl acetate 3:1) to give 38 mg of the title compound as a solid (yield: 67%).

Workup

  1. waitthe solution was left
  2. customThe acetic anhydride was evaporated under reduced pressure
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-34a585216d614b26b0ccea376aee14f5
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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