Cesium carbonate → HCID 69231272, compound

HRID 30396

Reaction equation

HRID 30396 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])=[O:3].I[CH2:11][CH2:12][CH2:13]I.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:1][S:2]([C:5]1([C:6]([O:8][CH3:9])=[O:7])[CH2:13][CH2:12][CH2:11]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 123141,3-DiiodopropaneHCID 2759918Methanesulfonylacetic acid methyl ester

Product 1

HCID 69231272HCID 69231272, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl methylsulfonylacetate (1.0 g, 6.6 mmol) in 20 mL of acetonitrile was added 1,3-diiodopropane (2.3 mL, 20 mmol) and cesium carbonate (6.4 g, 20 mmol). After stirring at room temperature for 2 h, the reaction was partitioned between water (50 mL) and ethyl acetate (100 mL). The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness, and the residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane to give methyl 1-methylsulfonylcyclobutanecarboxlate (1.0 g, 79%). δ 3.84 (s, 3H), 3.02 (s, 3H), 2.84-2.65 (m, 4H), 2.25-2.02 (m, 2H).

Workup

  1. customthe reaction was partitioned between water (50 mL) and ethyl acetate (100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customthe residue was purified by flash chromatography on silica gel eluting with 20 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c4ab329b32dc4ec78c61c1605479c0ea
Source dataset
uspto-grants-2008_09
Patent number
US07423067B2

Linked notes

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