Methanol → HCID 54281359, compound

HRID 275414Notes

Reaction equation

HRID 275414 reaction equation
[Cl:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[S:7][CH2:8][C:9]([OH:11])=[O:10].[CH3:12]O>>[Cl:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[S:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 887MethanolHCID 15237328HCID 15237328, compound

Product 1

HCID 54281359HCID 54281359, compound

Conditions

Temperature
5 °C

Procedure

trans-[(2-Chlorocyclopentyl)thio]acetic acid was dissolved in methanol (35 ml) and the solution was cooled to 5° C. with an ice bath. Hydrogen chloride gas was bubbled into the solution for 15 minutes. The methanol was removed with a gentle flush of nitrogen gas. The residue was dissolved in diethyl ether (50 ml) and washed twice with 50 ml of 15% sodium hydroxide, dried over anhydrous magnesium sulfate, filtered and concentrated to give the product as an oil. The structure was supported by NMR.

Workup

  1. customHydrogen chloride gas was bubbled into the solution for 15 minutes
  2. customThe methanol was removed with
  3. customa gentle flush of nitrogen gas
  4. dissolutionThe residue was dissolved in diethyl ether (50 ml)
  5. washwashed twice with 50 ml of 15% sodium hydroxide
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-311aaebd6a4c4577bffe237d6ebba167
Source dataset
uspto-grants-1995_02
Patent number
US05393764

Reaction notes

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