Sodium Bicarbonate → HCID 66727794, compound

HRID 2409178Notes

Reaction equation

HRID 2409178 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][CH:9]=[C:10]2[O:12][Si](C(C)(C)C)(C)C)=[O:5])[CH3:2].C([O-])(O)=[O:21].[Na+].[Mg].C1C=C(C(O)=O)C(C(O[O-])=O)=CC=1.C1C=C(C(O)=O)C(C(O[O-])=O)=CC=1.O.O.O.O.O.O.[Mg+2]>CO>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][CH:9]([OH:21])[C:10]2=[O:12])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 66727759HCID 66727759, compoundHCID 131731793HCID 131731793, compound

Product 1

HCID 66727794HCID 66727794, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (1RS,5SR,6RS)-2-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-ene-6-carboxylic acid ethyl ester (172 mmole) in MeOH (900 ml) was subsequently added NaHCO3 (33.25 g) and magnesium-monoperoxyphthalate (104.5 g) and stirring was continued at ambient temperature for 1 h. The mixture was filtered, the filtrate evaporated and the residue partitioned between saturated NaHCO3 (until gas evolution ceased) and dichloromethane. The organic layer was dried, evaporated and the residue dissolved in MeOH (750 ml). To the solution was subsequently added water (65 ml) and p-toluenesulfonic acid hydrate (3.44 g) and the mixture was stirred at 22° C. for 18 h. The mixture was evaporated, the residue partitioned between saturated NaHCO3 and dichloromethane, the organic layer was dried, evaporated and the residue dissolved in diethylether (350 ml) at reflux temperature. The solution was treated with n-pentane until the solution became cloudy, the mixture was slowly cooled to 0° C. and stirring was continued at 0° C. for 2 h. The suspension was filtered, and the residue dried to give the title compound (15.0 g) as white crystals.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customthe residue partitioned between saturated NaHCO3 (until gas evolution ceased) and dichloromethane
  4. customThe organic layer was dried
  5. customevaporated
  6. dissolutionthe residue dissolved in MeOH (750 ml)
  7. stirringthe mixture was stirred at 22° C. for 18 h
  8. customThe mixture was evaporated
  9. customthe residue partitioned between saturated NaHCO3 and dichloromethane
  10. customthe organic layer was dried
  11. customevaporated
  12. dissolutionthe residue dissolved in diethylether (350 ml)
  13. temperatureat reflux temperature
  14. additionThe solution was treated with n-pentane until the solution
  15. stirringstirring
  16. waitwas continued at 0° C. for 2 h
  17. filtrationThe suspension was filtered
  18. customthe residue dried

Sources & evidence

ORD record
ord-4939aecb89ca4a67ac15a63669a50d7f
Source dataset
uspto-grants-2014_08
Patent number
US08815881B2

Reaction notes

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