Acetone → HCID 14405954, compound

HRID 1650253Notes

Reaction equation

HRID 1650253 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].CC1C=CC(S(O[CH:17]2[O:21][C:20]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[S:19][CH2:18]2)(=O)=O)=CC=1.[CH3:36]C(C)=O>>[C:1]([S:3][CH2:36][CH:17]1[O:21][C:20]([CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[S:19][CH2:18]1)(=[O:4])[CH3:2]

Participants

4

Reactant 3

HCID 180AcetoneHCID 23053899HCID 23053899, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 14405954HCID 14405954, compoundYield 72%

Procedure

A stirred slurry of potassium thioacetate (0.50 g) in a solution of the tosylate produced in Example 62 (2.0 g, 0.0042 mol) in acetone (20 ml) was refluxed under nitrogen for 5 hrs. The reaction mixture was filtered and the filtrate concentrated on the rotary evaporator. The residue was dissolved in ethyl acetate, washed with water and dried over sodium sulfate. The drying agent was filtered, the solvent removed using the rotary evaporator and the residue chromatographed on silica gel using 10% ethyl acetate/hexane as eluent to give 1.1 g (72%) of the title compound as a light yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated on the rotary evaporator
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationThe drying agent was filtered
  7. customthe solvent removed
  8. customthe rotary evaporator
  9. customthe residue chromatographed on silica gel using 10% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-bbfc77cc6f8a441ea54a931c89df642f
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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