Ethyl Acetate → HCID 66740128, compound

HRID 1035704Notes

Reaction equation

HRID 1035704 reaction equation
[I-].C[S+](C)C.[CH3:6]C(C)([O-])C.[K+].[C:12]([O:16][C:17]([CH:19]=[C:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:36]=[CH:35][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(OCC)(=O)C>CS(C)=O>[CH2:33]([O:32][C:30]([C:29]1[CH:28]=[CH:27][C:26]([CH:23]2[CH2:24][CH2:25][C:20]3([CH:19]([C:17]([O:16][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:18])[CH2:6]3)[CH2:21][CH2:22]2)=[CH:36][CH:35]=1)=[O:31])[CH3:34]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 75127Trimethylsulfonium iodide2×HCID 23665647Potassium tert-butoxide2×HCID 66740127HCID 66740127, compound

Product 1

HCID 66740128HCID 66740128, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

5.11 g of trimethylsulfonium iodide (23.23 mmol, 4 eq.) are dissolved with stirring in 20 mL of DMSO in a 250 mL three-necked flask under a nitrogen atmosphere. 2.61 g of potassium tert-butoxide (23.23 mmol, 4 eq.) are added and the reaction medium is stirred for 3 hours. 2 g of ethyl 4-(4-tert-butoxycarbonylmethylenecyclohexyl)benzoate dissolved in 5 mL of DMSO are added and stirring is continued for 2 days. 2.56 g of trimethylsulfonium iodide (11.61 mmol, 2 eq.) are dissolved in 20 mL of DMSO in a 25 mL three-necked flask under a nitrogen atmosphere, and 1.0 g of potassium tert-butoxide (11.61 mmol, 2 eq.) is added with stirring. After 3 hours, this reaction medium is added to the 250 mL three-necked flask and stirring is continued for 18 hours. Ethyl acetate is added. The organic phase is washed with saturated aqueous ammonium chloride solution, dried over magnesium sulfate and filtered. The residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 50%. 0.159 g of tert-butyl 6-(4-ethoxycarbonylphenyl)spiro[2.5]octane-1-carboxylate is obtained.

Workup

  1. additionare added
  2. stirringstirring
  3. waitis continued for 2 days
  4. stirringwith stirring
  5. waitAfter 3 hours
  6. additionthis reaction medium is added to the 250 mL three-necked flask
  7. stirringstirring
  8. waitis continued for 18 hours
  9. washThe organic phase is washed with saturated aqueous ammonium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customThe residue is chromatographed on silica gel with a gradient of ethyl acetate in heptane ranging from 10% to 50%

Sources & evidence

ORD record
ord-6c489aa8d77c48b1a86f5d5ab039b1f4
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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