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

HRID 1966158Notes

Reaction equation

HRID 1966158 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. H NMR (CDCl3, 400 MHz) δ 5.07 (2H, h, J=6.8 Hz), 3.54 (4H, s), 1.23 (12H, d, J=6.8 Hz) ppm.

Workup

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

Sources & evidence

ORD record
ord-2a13090c981f4d908f0a8ebc045a16ec
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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