Propargyl bromide → HCID 54727674, compound

HRID 1579580Notes

Reaction equation

HRID 1579580 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[SH:10].[CH2:11](Br)[C:12]#[CH:13].[Br-].[NH+]1C=CC=CC=1>N1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[S:10][CH2:13][C:12]#[CH:11]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11309665Pyridinium bromideHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 54727674HCID 54727674, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 39.5 g. (0.250 mole) of 4-hydroxy-3-mercapto-6-methyl-2-pyrone in 250 ml. of pyridine was cooled to 15°C. in an ice bath. Propargyl bromide (29.7 g., 0.250 mole) was then added in one portion, causing the temperature of the reaction mixture to rise to 53°C. When the temperature began to subside, the flask was placed on the steam bath and heated at 80°C. for one hour, during which pyridinium bromide by-product precipitated. The reaction mixture was then cooled and poured into a mixture of ice and 500 ml. of concentrated hydrochloric acid. After this mixture had been kept cold in an ice bath for one hour, the crystalline product, which formed, was collected on a filter and dried; m.p. 143.5°-146°C., weight 27.2 g. More product was obtained by extraction of the filtrate with methylene chloride, giving a total yield of 41.9 g., (85 percent). Two recrystallizations (Darco) from ethanol afforded the pure 4-hydroxy-6-methyl-3-propargylthio- 2-pyrone as light tan crystals, m.p. 148°-149°C. (dec.).

Workup

  1. customto rise to 53°C
  2. customprecipitated
  3. temperatureThe reaction mixture was then cooled
  4. additionpoured into a mixture of ice and 500 ml
  5. customthe crystalline product, which formed
  6. customwas collected on
  7. filtrationa filter
  8. customdried
  9. customMore product was obtained by extraction of the filtrate with methylene chloride
  10. customgiving a total yield of 41.9 g
  11. customTwo recrystallizations (Darco) from ethanol

Sources & evidence

ORD record
ord-39dedc2a093346b09107be0a8617a65a
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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