Sodium Thiosulfate → HCID 69655716, compound

HRID 2216292Notes

Reaction equation

HRID 2216292 reaction equation
C(O[C:4](=[O:20])[C:5]([CH:8]1[CH:10]([C:11]2[C:19]3[O:18][CH2:17][O:16][C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH2:9]1)(O)C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH2:15]([O:16][C:17](=[O:18])[C:4](=[O:20])[CH2:5][CH:8]1[CH:10]([C:11]2[C:19]3[O:18][CH2:17][O:16][C:15]=3[CH:14]=[CH:13][CH:12]=2)[CH2:9]1)[CH3:14]

Participants

4

Reactant 2

HCID 24477Sodium ThiosulfateHCID 69655452HCID 69655452, compound

Product 1

HCID 69655716HCID 69655716, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13.9 g of 1,1,1-triacetoxy-1,1-dihydro-1,2-benzodioxol-3(1H)-one (Dess-Martin-Periodinane, cf. D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277) is added to a solution of 4.55 g of 3-(benzo[1,3]dioxol-4-yl)-cyclopropyl-2-hydroxypropionic acid ethyl ester in 205 ml of dichlormethane. After 6 hours at room temperature, the batch is added to a saturated solution of sodium thiosulfate and extracted with ether. It is washed with water, saturated bicarbonate solution and brine, dried (Na2SO4) and concentrated by evaporation. The residue is purified by column chromatography on silica gel with hexane-ethyl acetate (100: 0→80:20). 2.52 g of 3-(benzo[1,3]dioxol-4-yl)-cyclopropyl-2-oxopropionic acid ethyl ester is obtained. The latter is stirred in 84 ml of a solution of 1N sodium hydroxide solution in ethanol/water 2:1 at room temperature for 12 hours. The batch is concentrated in a vacuum, and the remaining solution is extracted with diethyl ether. The aqueous phase is acidified with 1 M hydrochloric acid and extracted with diethyl ether. After drying and concentration by evaporation, 2.2 g of 3-(benzo[1,3]dioxol-4-yl)-cyclopropyl-2-oxopropionic acid is obtained as a yellowish oil.

Workup

  1. extractionextracted with ether
  2. washIt is washed with water, saturated bicarbonate solution and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation
  5. customThe residue is purified by column chromatography on silica gel with hexane-ethyl acetate (100: 0→80:20)

Sources & evidence

ORD record
ord-5b7340dde9c242acb843b49814d0fd17
Source dataset
uspto-grants-2006_09
Patent number
US07112584B2

Reaction notes

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