Methyl propionate → HCID 52046095, compound

HRID 1907767Notes

Reaction equation

HRID 1907767 reaction equation
I[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.[N-:12]=[N+:13]=[N-:14].[Na+].[O:16]=[C:17]1[O:23][C@H:22]([C@H](CO)O)[C:20]([O-])=[C:18]1O.[Na+].C(OC)(=O)CC>CS(C)=O.[O-]S([O-])(=O)=O.[Cu+2].O>[O:7]1[C:6]2[CH:10]=[CH:11][C:3]([CH2:2][N:12]3[CH:20]=[C:18]([C:17]([O:23][CH3:22])=[O:16])[N:14]=[N:13]3)=[CH:4][C:5]=2[O:9][CH2:8]1

Participants

8

Reactant 4

HCID 11124Methyl propionateHCID 33557Sodium AzideHCID 11086556157766-09-1HCID 23667548Sodium Ascorbate

Product 1

HCID 52046095HCID 52046095, compoundYield 611.8%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

Compound 419 (1.72 g, 6.57 mmo) was dissolved in a 0.5 M solution of sodium azide 13.1 mL, 6.57 mmol) in DMSO (2 mL), stirred at room temperature overnight and quenched by pouring into a saturated solution of sodium thiosulfate. The compound was extracted with AcOEt, washed with brine, dried over MgSO4 and filtered to give a yellow solution. Water (2.5 mL) was then added followed by solid sodium ascorbate (130 mg, 0.657 mmol), methyl propionate (553 mg, 0.657 mmol) and 1M aq. CuSO4 solution (0.2 mL) to give a yellow solution. The reaction mixture was stirred overnight at room temperature to give a mustard-colored suspension. Water was added until a suspension formed, filtered, washed with water, and dried to generate the title compound 420 (1.05 g, 63% yield) as a mustard-colored solid.

Workup

  1. customquenched
  2. additionby pouring into a saturated solution of sodium thiosulfate
  3. extractionThe compound was extracted with AcOEt
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto give a yellow solution
  8. customto give a yellow solution
  9. stirringThe reaction mixture was stirred overnight at room temperature
  10. customto give a mustard-colored suspension
  11. customformed
  12. filtrationfiltered
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-92dd77cdcd2e4fbaba8f0b004b2028e6
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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