Propionic Acid → O-Propanoyloxymethyl S-Ethyl Carbonothioate

HRID 1609744Notes

Reaction equation

HRID 1609744 reaction equation
C([O-])(O)=O.[Na+].[C:6]([OH:10])(=[O:9])[CH2:7][CH3:8].[C:11](=[O:18])([S:15][CH2:16][CH3:17])[O:12][CH2:13]I>O.C(Cl)Cl>[C:11](=[O:18])([S:15][CH2:16][CH3:17])[O:12][CH2:13][O:9][C:6](=[O:10])[CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 1032Propionic AcidHCID 516892Sodium BicarbonateHCID 11436522(Ethylsulfanyl)(iodomethoxy)methanone

Product 1

HCID 14800950O-Propanoyloxymethyl S-Ethyl CarbonothioateYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of NaHCO3 (45 g, 536 mmol) in H2O (540 ml) is added TBA HSO4 (91.2 g, 268 mmol), propanoic acid (20.1 mL, 268 mmol), and CH2Cl2 (540 ml). Following stirring for 1 h at room temperature a solution of 5b (49.2 g, 200 mmol) in CH2Cl2 (100 mL) is added during 45 min keeping the temperature below 30° C. The stirring is continued for 11/2 h. The organic phase is separated, washed with H2O (200 mL), dried (MgSO4), and evaporated. The residue is stirred in Et2O (800 mL) during the night, filtered, and washed with Et2O (50 mL). The filtrate is evaporated and distilled to yield 38.0 g (98%) of 6cb, bp 71°-73° C./0.3 mbar.

Workup

  1. additionis added during 45 min
  2. customthe temperature below 30° C
  3. custom2 h
  4. customThe organic phase is separated
  5. washwashed with H2O (200 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. filtrationfiltered
  9. washwashed with Et2O (50 mL)
  10. customThe filtrate is evaporated
  11. distillationdistilled

Sources & evidence

ORD record
ord-97f0a9f208eb4a02a6d06645c44a43e8
Source dataset
uspto-grants-1995_03
Patent number
US05401868

Reaction notes

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