Tetrahydrofuran → 76825-10-0

HRID 1902860Notes

Reaction equation

HRID 1902860 reaction equation
C[Mg]Br.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2([N:18]([CH3:20])[CH3:19])[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.O1CCC[CH2:22]1.[Cl-].[NH4+]>CCOCC.C1C=CC=CC=1.O>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2([N:18]([CH3:20])[CH3:19])[CH2:12][CH2:13][C:14]([CH3:22])([OH:17])[CH2:15][CH2:16]2)=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 125956504-(4-Chlorophenyl)-4-(dimethylamino)cyclohexan-1-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 1271194976825-10-0

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To an ice-cooled solution of 10 ml. of 3 M methyl magnesium bromide in Et2O is added a solution of 1.25 g. (0.005 mole) of 4-(p-chlorophenyl)-4-(dimethylamino)cyclohexanone in 25 ml. of tetrahydrofuran. The mixture is stirred under nitrogen in the cold for one-half hour and then at room temperature for forty-eight hours. Following ice bath cooling there is added 20 ml. of saturated aqueous ammonium chloride, 10 ml. of water, 10 ml. diethyl ether and 25 ml. benzene. The organic layer is washed with 10 ml. water and 10 ml. brine and taken to dryness. The residue is chromatographed on a 1"×48" high pressure liquid chromatography column (elution with 3% MeOH in chloroform). Starting ketone is first eluted followed by a second material. Those fractions containing the second material are combined, concentrated to dryness and crystallized from CH3CN:H2O to yield 0.20 g. of the tertiary alcohol, melting point 119°-120°.

Workup

  1. waitat room temperature for forty-eight hours
  2. temperatureFollowing ice bath cooling there
  3. additionis added 20 ml
  4. washThe organic layer is washed with 10 ml
  5. customThe residue is chromatographed on a 1"×48" high pressure liquid chromatography column (elution with 3% MeOH in chloroform)
  6. washStarting ketone is first eluted
  7. additionThose fractions containing the second material
  8. concentrationconcentrated to dryness
  9. customcrystallized from CH3CN
  10. customH2O to yield 0.20 g

Sources & evidence

ORD record
ord-764e8a050554463090ba1e70748af37e
Source dataset
uspto-grants-1982_12
Patent number
US04366172

Reaction notes

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