1,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylate → 1,1-Bis(propan-2-yl) 3-oxocyclobutane-1,1-dicarboxylate

HRID 1692932

Reaction equation

HRID 1692932 reaction equation
C[O:2][C:3]1(OC)[CH2:6][C:5]([C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])([C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[CH2:4]1>FC(F)(F)C(O)=O.O.CCOC(C)=O>[O:2]=[C:3]1[CH2:6][C:5]([C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])([C:13]([O:15][CH:16]([CH3:17])[CH3:18])=[O:14])[CH2:4]1

Participants

4

Reactant 1

HCID 49133591,1-Bis(propan-2-yl) 3,3-dimethoxycyclobutane-1,1-dicarboxylate

Product 1

HCID 49133571,1-Bis(propan-2-yl) 3-oxocyclobutane-1,1-dicarboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22392675Trifluoroacetic acid waterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate (3 g, 0.01 mol) in 20 mL of trifluoroacetic acid-water (95:5) was stirred at 0° C. for 4 h. The reaction was diluted with EtOAc, washed with water, saturated NaHCO3 solution, and brine, dried over MgSO4 and evaporated to give crude product (2.4 g) as yellow oil, which was used directly in the next step.

Workup

  1. washwashed with water, saturated NaHCO3 solution, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-4794fde6e0f347b0b59e31bafa11ffc8
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Linked notes

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