Carbon Disulfide → Ethyl acetate hexane

HRID 1684026Notes

Reaction equation

HRID 1684026 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 415%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Powdered potassium hydroxide (1.75 g, 31.25 mmole) is dissolved in 3.0 ml methanol and carbon disulfide (2.85 g, 37.5 mmole) was added at 0° C. The reaction mixture is shaken vigorously and 3,5-dimethoxy-4-methoxymethoxyphenyloxirane (29) (3.0 g, 12.5 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, 2×30 ml ss NaCl, 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 was 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, 2×30 ml ss NaCl
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo to a yellow oil which
  7. customis purified by flash column chromatography

Sources & evidence

ORD record
ord-bdd8cd4f59e948138849007ebea7c3fb
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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