Cyclohexanone → HCID 13520354, compound

HRID 34476Notes

Reaction equation

HRID 34476 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[C:25]1(=[O:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[Cl-].[NH4+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]([N:11]([CH3:12])[CH3:13])=[O:10])[C:25]2([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 7967CyclohexanoneHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 46315952-(4-bromophenyl)-N,N-dimethylacetamideHCID 178418339Butyllithium

Product 1

HCID 13520354HCID 13520354, compound

Conditions

Temperature
-78 °C

Procedure

4-bromo-N,N-dimethylbenzene acetamide (15 g, 0.06 mole) was added to dry T.H.F. (250 ml) and the solution cooled to -78° C. under nitrogen. Straight chain butyl lithium in hexane (43.3 ml, 0.06 mole) was added dropwise, the temperature being maintained below -70° C. throughout. An orange coloured precipitate formed. After addition, the reaction mixture was maintained near -70° C. for 20 minutes and cyclohexanone (7.5 ml, 0.07 mole) was added. After a further 50 minutes at -78° C. the reaction mixture was poured into stirring saturated ammonium chloride solution. The layers were separated and the aqueous layer extracted with diethyl ether. The combined organic solution was washed with brine, dried over magnesium sulfate and evaporated. The product crystallised and was filtered with isopropanol (9.8 g, m.p. 140 °-144° C.).

Workup

  1. customto dry T.H.F
  2. temperaturethe temperature being maintained below -70° C. throughout
  3. customformed
  4. additionAfter addition
  5. temperaturethe reaction mixture was maintained near -70° C. for 20 minutes
  6. additionAfter a further 50 minutes at -78° C. the reaction mixture was poured
  7. customThe layers were separated
  8. extractionthe aqueous layer extracted with diethyl ether
  9. washThe combined organic solution was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. customThe product crystallised
  13. filtrationwas filtered with isopropanol (9.8 g, m.p. 140 °-144° C.)

Sources & evidence

ORD record
ord-67d83037f187478c89404183cfcb952e
Source dataset
uspto-grants-1988_08
Patent number
US04761501

Reaction notes

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