Succinic anhydride → HCID 11117509, compound

HRID 1429554Notes

Reaction equation

HRID 1429554 reaction equation
[O:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=[O:7].[CH3:8][Si:9]([CH3:14])([CH3:13])[CH2:10][CH2:11][OH:12]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[O:6]=[C:5]([O:12][CH2:11][CH2:10][Si:9]([CH3:14])([CH3:13])[CH3:8])[CH2:4][CH2:3][C:2]([OH:7])=[O:1]

Participants

6

Reactant 2

HCID 7922Succinic anhydrideHCID 180132-(Trimethylsilyl)ethanol

Product 1

HCID 11117509HCID 11117509, compoundYield 118%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dihydrofuran-2,5-dione (8.0 g, 80 mmol) and 2-(trimethylsilyl)ethanol (5 g, 42.3 mmol) were dissolved in dry toluene (80 mL), followed by addition of DMAP (0.517 g, 4.23 mmol). The mixture was heated to reflux for 14 h. The mixture was cooled to rt, diluted with EtOAc (50 mL) and washed with aq. HCl (1 N, 3×30 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to afford crude product as a white semi-solid (10.9 g, purity 85% as determined by 1H NMR, 100% yield), which is used in next reaction without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 14 h
  3. washwashed with aq. HCl (1 N, 3×30 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a21eac986ac34459988254dc73f0fff7
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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