Methanethiol → HCID 57117933, compound

HRID 1955439Notes

Reaction equation

HRID 1955439 reaction equation
C[O-].[Na+].[Na].[CH3:5][SH:6].[CH2:7]1[O:16][C:10]([CH2:12][CH2:13][CH2:14]Cl)([CH3:11])[O:9][CH2:8]1>C1(C)C=CC=CC=1.CO>[CH2:7]1[O:16][C:10]([CH2:12][CH2:13][CH2:14][S:6][CH3:5])([CH3:11])[O:9][CH2:8]1

Participants

7

Reactant 4

HCID 878Methanethiol2×HCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolaneHCID 5360545Sodium2×HCID 10942334Sodium Methoxide

Product 1

HCID 57117933HCID 57117933, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of sodium methoxide prepared by slowly adding 2.4 g (54 mmol) of sodium to 40 mL of methanol was added 4.8 g (48 mmol) of methylmercaptan followed by 6.6 g (40 mmol) of 5-chloro-2-pentanone ethylene ketal. The mixture was refluxed for 4 h and an additional 50 mmol each of sodium and methylmercaptan was added and then refluxed an additional 4 hours to complete the reaction. 50 mL of toluene was added and the mixture washed twice with 10 mL of 1N sodium hydroxide. The toluene layer was dried over magnesium sulfate and evaporated to give 7.1 g of 5-methylthio-2-pentanone ethylene ketal. This was stirred in 60 mL of 70% trifluoroacetic acid for 24 h at room temperature. The mixture was neutralized with sodium carbonate and extracted with 200 mL of ether. The ether extract was dried and evaporated to yield 3.5 g of the desired ketone as an oil.

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. temperaturerefluxed an additional 4 hours
  3. customthe reaction
  4. washthe mixture washed twice with 10 mL of 1N sodium hydroxide
  5. dry with materialThe toluene layer was dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-cab48e3d7a2f4ca9b5b5dfa37b7b81eb
Source dataset
uspto-grants-1998_07
Patent number
US05775329

Reaction notes

Loading…