Acetone → HCID 14405954, compound

HRID 1383159Notes

Reaction equation

HRID 1383159 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-4668587199af43f2bf9d7f4ce0a8a7b5
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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