Carbon Disulfide → Ethyl acetate hexane

HRID 1684027Notes

Reaction equation

HRID 1684027 reaction equation
[OH-].[K+].[C:3](=S)=S.CO[C:8]1[CH:9]=[C:10](C2CO2)[CH:11]=[C:12](OC)[C:13]=1[O:14][CH2:15][O:16]C>CO>[CH3:10][CH2:9][CH2:8][CH2:13][CH2:12][CH3:11].[C:15]([O:14][CH2:13][CH3:8])(=[O:16])[CH3:3]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 54128898HCID 54128898, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 207.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Powdered potassium hydroxide (3.50 g, 62.50 mmole) is dissolved in 6.0 ml methanol and carbon disulfide (5.70 g, 75.0 mmole) is added at 0° C. The reaction mixture is shaken vigorously and 3,5-dimethoxy-4-methoxymethoxyphenyloxirane (29) (6.0 g, 25.0 mmole) is added. The reaction is allowed to warm to room temperature at which point the reaction starts to reflux. The reaction is stirred at room temperature for 24 hours, and is quenched with ethyl acetate and 10% NaOH. The organic layer is washed with 3×40 ml 10% NaOH, 1×30 ml H2O, and 2×30 ml ss NaCI. The ethyl acetate is reduced to 10 ml and 30 ml methanol along with 10 ml 5.0M methanolic HCl. The reaction is stirred for three hours, quenched with 100 ml H2O, extracted with ethyl acetate, dried over MgSO4, and evaporated in vacuo to a yellow oil which is purified by flash column chromatography using 2:1 hexane/ethyl acetate. The product is recrystallized from hexane/ethyl acetate (4.52 g, 63% yield).

Workup

  1. temperatureto reflux
  2. stirringThe reaction is stirred at room temperature for 24 hours
  3. customis quenched with ethyl acetate and 10% NaOH
  4. washThe organic layer is washed with 3×40 ml 10% NaOH, 1×30 ml H2O, and 2×30 ml ss NaCI
  5. stirringThe reaction is stirred for three hours
  6. customquenched with 100 ml H2O
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over MgSO4
  9. customevaporated in vacuo to a yellow oil which
  10. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-1dc4f9bebe8d46dc9d64fcd1e9dce282
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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