Dimethylformamide → HCID 15407837, compound

HRID 2273715Notes

Reaction equation

HRID 2273715 reaction equation
CN(C)[CH:3]=[O:4].P(Br)(Br)[Br:7].[CH3:10][C:11]1([CH3:18])[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Br:7][C:13]1[CH2:12][C:11]([CH3:18])([CH3:10])[CH2:16][CH2:15][C:14]=1[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24614Phosphorus tribromideHCID 76322Cyclohexanone, 3,3-dimethyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 15407837HCID 15407837, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
70 °C

Procedure

N,N-dimethylformamide (18.41 ml) was taken up in chloroform (64 ml) and the resulting solution was cooled in an ice bath. Phosphorus tribromide (20.18 ml) was added dropwise over 15 minutes. The resulting suspension was then heated to 70° C. for 30 minutes. A solution of 3,3-dimethylcyclohexanone (10 g) in chloroform (21 ml) was added dropwise over 30 minutes. The mixture was stirred at 70° C. for another 2 hours. The mixture was then allowed to cool to room temperature. The solution was cautiously poured over ice. Solid sodium bicarbonate was added to neutralize acid. The mixture was extracted three times with ether, and the extracts were washed with water and brine and dried (MgSO4). The solvent was removed under vacuum, and the crude material was flushed through a silica plug with ether as the eluent. After concentration, the crude material was dissolved in methanol. Sodium borohydride (1.757 g) was added cautiously. The resulting mixture was stirred at room temperature overnight, and diluted with ethyl acetate. The mixture was washed with water and brine and dried (MgSO4). The solvent was removed under vacuum, and the residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to 100% ethyl acetate.

Workup

  1. temperaturethe resulting solution was cooled in an ice bath
  2. temperatureto cool to room temperature
  3. additionThe solution was cautiously poured over ice
  4. extractionThe mixture was extracted three times with ether
  5. washthe extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed under vacuum
  8. customthe crude material was flushed through a silica plug with ether as the eluent
  9. concentrationAfter concentration
  10. dissolutionthe crude material was dissolved in methanol
  11. additionSodium borohydride (1.757 g) was added cautiously
  12. stirringThe resulting mixture was stirred at room temperature overnight
  13. additiondiluted with ethyl acetate
  14. washThe mixture was washed with water and brine
  15. dry with materialdried (MgSO4)
  16. customThe solvent was removed under vacuum
  17. customthe residue was purified by flash chromatography
  18. washeluting with 20% ethyl acetate in hexanes to 100% ethyl acetate

Sources & evidence

ORD record
ord-691b85589d5f4873bfe07797b96551fe
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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