Potassium Acetate → HCID 178501333, compound

HRID 422685Notes

Reaction equation

HRID 422685 reaction equation
[C:1]([O-])(=[O:3])[CH3:2].[K+].[CH3:6][O:7][C:8]([C@H:10]1[CH2:13][C@@H:12]([O:14]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:11]1)=[O:9]>CN(C=O)C>[CH3:6][O:7][C:8]([C@H:10]1[CH2:11][C@H:12]([O:14][C:1](=[O:3])[CH3:2])[CH2:13]1)=[O:9]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 178501347HCID 178501347, compound

Product 1

HCID 178501333HCID 178501333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of potassium acetate (16.9 g, 172 mmol) and cis-3-(toluene-4-sulfonyloxy)-cyclobutanecarboxylic acid methyl ester (9.8 g, 34 mmol; trans/cis=1:5) in dry DMF (50 mL) was heated to 120° C. for 21 h. DMF was partially distilled off (≈30 mL), water was added, and the mixture was extracted with EtOAc (6×50 mL). The combined organic layers were washed with water (2×), brine, dried over MgSO4, filtered and concentrated to give the title compound as brown oil, trans/cis=5:1 based on 1H NMR. The material thus obtained was used without further purification.

Workup

  1. distillationDMF was partially distilled off (≈30 mL), water
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc (6×50 mL)
  4. washThe combined organic layers were washed with water (2×), brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fa3dbec6448f44ad810272139b88dc49
Source dataset
uspto-grants-2012_01
Patent number
US08101613B2

Reaction notes

Loading…