Water → 2,5-Dimethyl-3-thioacetylfuran

HRID 129971Notes

Reaction equation

HRID 129971 reaction equation
O[CH:2]([CH3:8])[C:3]#[C:4][C:5](=[O:7])[CH3:6].[C:9](O)(=[S:11])[CH3:10].O>C(Cl)Cl.S(=O)(=O)(O)O>[CH3:8][C:2]1[O:7][C:5]([CH3:6])=[CH:4][C:3]=1[C:9](=[S:11])[CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 108986755-Hydroxy-3-hexyn-2-oneHCID 178418634HCID 178418634, compound

Product 1

HCID 193709452,5-Dimethyl-3-thioacetylfuran

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

5.61 g of 5-hydroxyhex-3-yn-2-one [prepared according to A. F. Thomas et al., Tet. Let. 27, 505, (1986)] in 50 ml of methylene chloride are added dropwise while stirring within 15 min. to a mixture of 11.42 g of thioacetic acid in 50 ml of methylene chloride and 100 ml of 2N sulphuric acid. After leaving to stand at room temperature for 2 hours the mixture is heated to 40° C. and stirred at 40° C. for a further 4 hrs. The reaction mixture is poured into 100 ml of H2O and extracted 2× with 100 ml of methylene chloride. The organic phases, dried over MgSO4, are concentrated and fractionally distilled in a high vacuum (65° C./0.2 mbar). There are obtained 5.7 g (67% of theory) of a yellow liquid.

Workup

  1. customAfter leaving
  2. extractionextracted 2× with 100 ml of methylene chloride
  3. dry with materialThe organic phases, dried over MgSO4
  4. concentrationare concentrated
  5. distillationfractionally distilled in a high vacuum (65° C./0.2 mbar)
  6. customThere are obtained 5.7 g (67% of theory) of a yellow liquid

Sources & evidence

ORD record
ord-d431184b61524a78bc1fcfd77aaa7f68
Source dataset
uspto-grants-1995_11
Patent number
US05470991

Reaction notes

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