Hydrochloric Acid → HCID 73853845, compound

HRID 1243856Notes

Reaction equation

HRID 1243856 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[N:26](OC(C)(C)C)=[O:27].Cl>C(O)(C)(C)C.C(OCC)C>[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][C:11](=[N:26][OH:27])[C:10](=[O:13])[CH:9]=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 1382802-Cyclohexen-1-one, 4,4-diphenyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 73853845HCID 73853845, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent2×

Conditions

Temperature
30 °C

Procedure

A solution of 10.1 g of 4,4-diphenylcyclohex-2-enone in 60 cm3 of tert-butanol is added to a solution of 6.5 g of potassium tert-butoxide in 50 cm3 of tert-butanol at a temperature in the region of 30° C. After stirring for about 15 minutes at a temperature in the region of 30° C., this solution is added dropwise to 14 cm3 of tert-butyl nitrite. The reaction mixture is stirred at a temperature in the region of 20° C. for 2 hours. 100 cm3 of aqueous 3 M hydrochloric acid solution and 100 cm3 of diethyl ether are then added to the preceding mixture at a temperature in the region of 20° C. After separation of the phases by settling, the aqueous phase is extracted with 100 cm3 of diethyl ether. The combined organic phases are washed with three times 100 cm3 of saturated aqueous sodium bicarbonate solution and then with 100 cm3 of saturated aqueous sodium chloride solution, and then dried over magnesium sulphate, filtered and concentrated. After concentrating to dryness under reduced pressure (13 kPa), the residue is purified by flash chromatography on a column of silica (eluent: cyclohexane/ethyl acetate (80/20 by volume)]. 2.23 g of 5,5-diphenylcyclohex-3-ene-1,2-dione 1-oxime are thus obtained in the form of a yellow foam, which is used without further modification for subsequent syntheses and the characteristics of which are as follows:

Workup

  1. stirringThe reaction mixture is stirred at a temperature in the region of 20° C. for 2 hours
  2. customAfter separation of the phases
  3. extractionthe aqueous phase is extracted with 100 cm3 of diethyl ether
  4. washThe combined organic phases are washed with three times 100 cm3 of saturated aqueous sodium bicarbonate solution
  5. dry with materialwith 100 cm3 of saturated aqueous sodium chloride solution, and then dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationAfter concentrating to dryness under reduced pressure (13 kPa)
  9. customthe residue is purified by flash chromatography on a column of silica (eluent

Sources & evidence

ORD record
ord-4e586b2f39c74edd9e8c0cea05d0193e
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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