Sodium Sulfite → HCID 68671607, compound

HRID 2192894Notes

Reaction equation

HRID 2192894 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[CH:18][CH:19]2[CH2:23][CH2:22][C:21]3([O:28][CH2:27][C:26]([CH3:30])([CH3:29])[CH2:25][O:24]3)[CH2:20]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8][CH:9]1[CH2:11][CH2:10]1.[OH:31]OS([O-])=O.[K+].C(=O)([O-])O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CO.C1COCC1.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:12](=[CH:18][CH:19]2[CH2:23][CH2:22][C:21]3([O:24][CH2:25][C:26]([CH3:29])([CH3:30])[CH2:27][O:28]3)[CH2:20]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH:9]1[CH2:11][CH2:10]1)=[O:31]

Participants

9

Reactant 4

HCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 68671175HCID 68671175, compound

Product 1

HCID 68671607HCID 68671607, compoundYield 97.5%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-[3-bromo-4-(cyclopropylsulfanyl)phenyl]-3-(8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl)acrylate (1.63 g, (E)/(Z)-mixture) was dissolved in methanol (16.3 mL)-THF (16.3 mL) mixed solvent, followed by ice-cooling. To this solution was added a solution of Oxone (registered trademark, 2.43 g) in water (16.3 mL), followed by warming to room temperature and stirring for 1 hour. A saturated aqueous sodium hydrogen carbonate solution was added thereto, and further added a 1 M aqueous sodium sulfite solution and ethyl acetate. The organic layer was separated and the aqueous layer was then extracted with ethyl acetate. The organic layer was further washed with a saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain ethyl 2-[3-bromo-4-(cyclopropylsulfinyl)phenyl]-3-(8,8-dimethyl-6,10-dioxaspiro[4.5]dec-2-yl)acrylate (1.64 g) as an (E)/(Z)-mixture of olefin.

Workup

  1. additionmixed solvent
  2. temperaturecooling
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was then extracted with ethyl acetate
  5. washThe organic layer was further washed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-23fb1c3b9c8d46d3b96c586fbfdcf0c0
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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