Hexanal → HCID 19823724, compound

HRID 1650939Notes

Reaction equation

HRID 1650939 reaction equation
[CH:1]([N-:4][CH:5](C)C)(C)C.[Li+].[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].C(N[CH:18]([CH3:20])C)(C)C.[CH:21](=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[Cl-:28].[NH4+].C[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O1CCCC1>[Cl:28][C:9]1[CH:20]=[CH:18][C:12]([C:23]2([CH:22]([N:4]([CH3:1])[CH3:5])[C:21](=[O:27])[CH2:35][CH2:34][CH2:33][CH2:32][CH3:31])[CH2:26][CH2:25][CH2:24]2)=[CH:11][CH:10]=1

Participants

8

Reactant 6

HCID 6184HexanalHCID 7912DiisopropylamineHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 19823724HCID 19823724, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2-[1-(4-chlorophenyl)cyclobutyl]-2-dimethylaminoacetontrile (15 g prepared as described in Example A) in dry tetrahydrofuran (50 ml) was added with stirring at -70° C. over a period of 35 minutes to a solution of lithium diisopropylamide [prepared by the addition of a 2.7M solution of butyllithium in hexane (37 ml) to a solution of diisopropylamine (15 ml) in dry tetrahydrofuran (45 ml) at 5° C.] followed by stirring for 1 hour at a temperature below 5° C. A portion (ca. 100 ml) of the above solution was cooled to -70° C. A solution of hexanal (12 ml) in dry tetrahydrofuran (20 ml) was added over 10 minutes and the mixture stirred for 1 hour at -70° C. The temperature was maintained at -70° C. whilst excess saturated ammonium chloride solution was added and the mixture was then allowed to warm to ambient temperature. The mixture was extracted with ether and the dried extract evaporated to give an oil which was distilled (160°-170° C./1 mm Hg) eliminating hydrogen cyanide. The distillate was dissolved in excess 2N hydrochloric acid to give an aqueous solution which was washed with ether, basified and extracted with ether. The extract was dried and the solvent removed by evaporation to give an oil which was distilled in a Buchi Kugelrohr apparatus (250°/1 mm) to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylaminoheptan-2-one.

Workup

  1. stirringthe mixture stirred for 1 hour at -70° C
  2. additionwas added
  3. extractionThe mixture was extracted with ether
  4. extractionthe dried extract
  5. customevaporated
  6. customto give an oil which
  7. distillationwas distilled (160°-170° C./1 mm Hg)
  8. dissolutionThe distillate was dissolved in excess 2N hydrochloric acid
  9. customto give an aqueous solution which
  10. washwas washed with ether
  11. extractionextracted with ether
  12. customThe extract was dried
  13. customthe solvent removed by evaporation
  14. customto give an oil which
  15. distillationwas distilled in a Buchi Kugelrohr apparatus (250°/1 mm)

Sources & evidence

ORD record
ord-ef937363952a483ba23c37562c1e0447
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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