Ethanol → HCID 86742688, compound

HRID 2292154Notes

Reaction equation

HRID 2292154 reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[C:3]=1[CH2:9][C:10]([O-:12])=[O:11].[SH:13][CH2:14][C:15]([O:17]CC)=O.[CH3:20][C:21](C)([O-:23])C.[K+].[CH2:26](O)[CH3:27]>>[CH2:21]([O:23][C:2]1[CH:7]([S:13][CH:14]=[C:15]=[O:17])[CH2:6][CH2:5][C:4](=[O:8])[C:3]=1[CH2:9][C:10]([O:12][CH2:26][CH3:27])=[O:11])[CH3:20]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 12185Ethyl ThioglycolateHCID 20070494HCID 20070494, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 86742688HCID 86742688, compound

Procedure

To a solution of α-(2-chloro-6-oxocyclohex-1-enyl)acetate (700 g) in anhydrous ethanol (2.1L) is added ethyl mercaptoacetate (410 g). Then to this solution is added at 5° a solution of potassium t-butoxide (381 g) in anhydrous ethanol (1.8L) dropwise over a period of 1.5 hours. This is stirred for an additional 2 hours at this temperature and then kept at room temperature overnight. The solvent is removed in vacuo and the residue is mixed with ethyl ether (3L) and water. The layers are separated and the organic layer is washed with water (2×400 mL), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo to yield ethyl α-(2-ethoxy-carbonylmethylthio-6-oxocyclohex-1-enyl)acetate as a light yellow oil.

Workup

  1. waitkept at room temperature overnight
  2. customThe solvent is removed in vacuo
  3. additionthe residue is mixed with ethyl ether (3L) and water
  4. customThe layers are separated
  5. washthe organic layer is washed with water (2×400 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-a7bc26bd1cc44bc6b4e849ff501a185e
Source dataset
uspto-grants-1989_01
Patent number
US04801605

Reaction notes

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