Acetic Acid → Z-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-one

HRID 392815Notes

Reaction equation

HRID 392815 reaction equation
[CH3:1][C:2]1([CH3:29])[O:6][C:5](=[O:7])/[C:4](=[CH:8]/[C:9]([O:11][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:10])/[O:3]1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:29])[O:6][C:5](=[O:7])/[C:4](=[CH:8]/[C:9]([OH:11])=[O:10])/[O:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 21947558(Z)-2,2-Dimethyl-5-(tert-butyldiphenylsilyloxycarbonyl-methylene)-1,3-dioxolan-4-one

Product 1

HCID 11636888Z-2,2-dimethyl-5-carboxymethylene-1,3-dioxolan-4-oneYield 85.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of pure (Z)-2,2 dimethyl-5-(t-butyldiphenylsilyloxycarbonylmethylene)-1,3-dioxolan-4-one (2.80 g, 6.82 mmol) in tetrahydrofuran (40 ml) was treated at 22° C. with acetic acid (2 ml) followed by 6.8 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran. After 15 minutes at 22° C., the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried (magnesium sulfate). The solvent was concentrated under reduced pressure and the residue was triturated with toluene to give 1.00 g (85%) of the title compound as a white crystalline material: mp 203-204° C. (dec.). IR (KBr) v max (cm −1): 1805, 1707 and 1662. 1H NMR (400 MHz, CDCl3) δ: 1.78 (s, 6), 5.89 (s, 1). Anal. calcd for C7H8O5: C, 48.84; H, 4.68. found: C, 48.84; H, 4.65.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe residue was triturated with toluene

Sources & evidence

ORD record
ord-f9795dc884644b4797b29dba8d60b1d3
Source dataset
uspto-grants-2004_10
Patent number
US06803378B2

Reaction notes

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