Diethyl Sulfate → HCID 14330446, compound

HRID 2292157Notes

Reaction equation

HRID 2292157 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([S:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:4][CH:3]=1.S(OCC)(O[CH2:25][CH3:26])(=O)=O.CC(C)([O-])C.[K+]>C(O)C>[CH2:25]([O:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([S:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:4][CH:3]=1)[CH3:26]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 14330445HCID 14330445, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 14330446HCID 14330446, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-hydroxy-2-(ethoxycarbonylmethylthio)-phenylacetate (20.0 g) in anhydrous ethanol (200 mL) is added diethyl sulfate (10.3 g). To this is added in portions solid potassium t-butoxide (7.52 g), keeping the temperature below 30° with a cold-water bath. After stirring overnight at room temperature, the solvent is removed in vacuo and the residue is mixed with ether and water. The layers are separated and the organic layer is washed with ice-cold sodium hydroxide (0.5N, 40 mL) to remove starting material. The ether layer is washed with water to neutrality, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo to give (as shown by NMR) ethyl 6-ethoxy-2-(ethoxycarbonylmethylthio)-phenylacetate as an oil.

Workup

  1. customthe temperature below 30°
  2. customthe solvent is removed in vacuo
  3. additionthe residue is mixed with ether and water
  4. customThe layers are separated
  5. washthe organic layer is washed with ice-cold sodium hydroxide (0.5N, 40 mL)
  6. customto remove
  7. washThe ether layer is washed with water to neutrality
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-e147801ec47a4424b1d5b18c37318e29
Source dataset
uspto-grants-1989_01
Patent number
US04801605

Reaction notes

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