Water → HCID 178525582, compound

HRID 1461995Notes

Reaction equation

HRID 1461995 reaction equation
C(=O)(O)[O-].[Na+].[C@H:6]1([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10][C@H:9]([C:12]([O-:14])=[O:13])[CH2:8][CH2:7]1.[K+].O.[CH:27](Cl)(Cl)[Cl:28]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C@H:6]1([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:7][CH2:8][C@H:9]([C:12]([O:14][CH2:27][Cl:28])=[O:13])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 178525736HCID 178525736, compound

Product 1

HCID 178525582HCID 178525582, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

To a mixture of 3.06 g (0.036 mole) sodium bicarbonate, 5.46 g (0.018 mole) potassium benzyl trans-1,4-cyclohexanedicarboxylate, 50 ml water and 500 ml chloroform is added 6.17 g (0.018 mole) tetrabutylammonium hydrogen sulfate and the mixture is stirred at room temperature overnight. The layers are separated. The aqueous layer is extracted twice with chloroform and the combined chloroform layers are dried and evaporated to dryness. The resulting tetrabutylammonium salt is taken up in methylene chloride (20 ml) and the solution added dropwise to 20 ml of bromochloromethane at 0° C. The resulting mixture is stirred at ambient temperature for 70 hours, the solvent evaporated and ethyl acetate added to the residue. The precipitated tetrabutylammonium bromide is removed by filtration, the filtrate dried (Na2SO4) and evaporated in vacuo to obtain 5 g (91%) of crude product. Purification by silica gel chromatography, eluting with 1:3 ethyl ether/hexane gave 1.9 g (35%) of the desired product as an oil. 1H-NMR (CDCl3) ppm (delta): 1.0-2.4 (m, 10H), 5.1 (s, 2H), 5.7 (s, 2H), 7.3 (s, 5H).

Workup

  1. customThe layers are separated
  2. extractionThe aqueous layer is extracted twice with chloroform
  3. dry with materialthe combined chloroform layers are dried
  4. customevaporated to dryness
  5. additionthe solution added dropwise to 20 ml of bromochloromethane at 0° C
  6. stirringThe resulting mixture is stirred at ambient temperature for 70 hours
  7. customthe solvent evaporated
  8. additionethyl acetate added to the residue
  9. customThe precipitated tetrabutylammonium bromide is removed by filtration
  10. dry with materialthe filtrate dried (Na2SO4)
  11. customevaporated in vacuo
  12. customto obtain 5 g (91%) of crude product
  13. customPurification by silica gel chromatography
  14. washeluting with 1:3 ethyl ether/hexane

Sources & evidence

ORD record
ord-4c1e0200c1ac4ebca200d3ef99c26881
Source dataset
uspto-grants-1984_07
Patent number
US04457924

Reaction notes

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