Cyclohexanone → HCID 10541879, compound

HRID 2096494Notes

Reaction equation

HRID 2096494 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.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:12]1([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 10541879HCID 10541879, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In a 50 mL round bottom flask was added 1-(5-bromo-2-hydroxyphenyl)ethanone (2.0 g, 9.3 mmol), followed by cyclohexanone (0.96 mL, 9.3 mmol). MeOH (20 mL) was added to give a clear solution followed by pyrrolidine (1 mL). A condenser was attached to the flask, and the resulting solution was heated at 60° C. overnight. MeOH was removed and the residue was redissolved in EtOAc (30 mL), washed with 1 N NaOH (10 mL) and 1 N HCl (10 mL), and then dried over Na2SO4. Solvent was removed in vacuo to give 6-bromospiro[chroman-2,1′-cyclohexan]-4-one (2.25 g, 82%), which is used for the next step without purification.

Workup

  1. customto give a clear solution
  2. customA condenser was attached to the flask
  3. customMeOH was removed
  4. dissolutionthe residue was redissolved in EtOAc (30 mL)
  5. washwashed with 1 N NaOH (10 mL) and 1 N HCl (10 mL)
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-9f0cac29155f423992987bbd30b3aa3b
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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