3-Methylcyclohexanone → HCID 58424286, compound

HRID 1408687Notes

Reaction equation

HRID 1408687 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:12][CH:13]1[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:15]1([CH2:16][CH2:17][CH2:18][CH:13]([CH3:12])[CH2:14]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 115673-MethylcyclohexanoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58424286HCID 58424286, compoundYield 124.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-(5-bromo-2-hydroxy-phenyl)-ethanone (10 g, 46.7 mmol), 3-methylcyclohexanone (10.5 g, 93.4 mmol) and pyrrolidine (6.3 g, 88.8 mmol) in methanol (200 mL) was stirred overnight. The reaction mixture was concentrated in vacuo, and then H2O was added. The resulting solution was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 6-bromo-3′-methylspiro[chroman-2,1′-cyclohexan]-4-one (18 g, 100%). 1HNMR (CDCl3): 0.86 (m, 3H), 0.91 (m, 2H), 1.02 (m, 2H), 1.30 (m, 2H), 1.52 (m, 2H), 1.65 (m, 4H), 1.80 (m, 7H), 2.01 (m, 4H), 2.22 (m, 1H), 2.48 (m, 1H), 2.60 (s, 2H), 2.72 (t, 3H), 6.81 (m, 1H), 7.50 (m, 1H), 7.91 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionH2O was added
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46301e29e721407ea7e1d870ca7d7255
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

Loading…