2(3H)-Furanone, 3-bromodihydro- → 3-(4-Chlorobenzenesulfonyl)-dihydro-furan-2-one

HRID 1924858Notes

Reaction equation

HRID 1924858 reaction equation
Br[CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O-:18])=[O:17])=[CH:12][CH:11]=1>C(O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH:2]2[CH2:7][CH2:6][O:5][C:3]2=[O:4])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 954632(3H)-Furanone, 3-bromodihydro-HCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 567327883-(4-Chlorobenzenesulfonyl)-dihydro-furan-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of α-bromo-γ-butyrolactone (1.58 g; 9.62 mmol) and 4-chlorobenzenesulfinic acid sodium salt (2.39 g; 12.03 mmol) in ethanol (75 mL) was heated at 65° C. for 10 hours and the volatiles removed in vacuo. The residue was diluted with ethyl acetate and filtered. Removal of the volatiles from the filtrate provided as residue which was purified by silica gel chromatography using ethyl acetate and hexanes as the eluent. Removal of the volatiles from the product-rich fractions provided 1.58 g of the desired product. 1H NMR (CDCl3) δ 7.89 (d, 2H), 7.58 (d, 2H), 4.54 (m, 1H), 4.42 (m, 1H), 4.03 (dd, 1H), 3.07 (m, 1H), 2.77 (m, 1H).

Workup

  1. customthe volatiles removed in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. filtrationfiltered
  4. customRemoval of the volatiles from the filtrate
  5. customprovided as residue which
  6. customwas purified by silica gel chromatography
  7. customRemoval of the volatiles from the product-rich fractions

Sources & evidence

ORD record
ord-7e8de288cbde4db09de054212f85d252
Source dataset
uspto-grants-2012_05
Patent number
US08178568B2

Reaction notes

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