4-tert-Butylcyclohexanone → HCID 58423937, compound

HRID 2096579Notes

Reaction equation

HRID 2096579 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]([CH:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:11][C:19]1([CH2:20][CH2:21][CH:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:17][CH2:18]1)[CH2:9][C:8]2=[O:10]

Participants

5

Reactant 3

HCID 73924-tert-ButylcyclohexanoneHCID 31268PyrrolidineHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 58423937HCID 58423937, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a 50 mL round bottom flask is added 1-(5-bromo-2-hydroxyphenyl)ethanone (2.0 g, 9.3 mmol), followed by 4-tert-butylcyclohexanone (1.43 g, 9.3 mmol). MeOH (20 mL) is added to give a clear solution, followed by pyrrolidine (1 mL). A condenser is attached to the RB flask, and the resulting solution is heated at 60° C. for two hours. MeOH is removed and the residue is redissolved in EtOAc (30 mL), washed with 1 N NaOH (10 mL), and 1 N HCl (10 mL), and dried over Na2SO4. Solvent is removed in vacuo to give 6-bromo-4′-t-butylspiro[chroman-2,1′-cyclohexan]-4-one (2.41 g, 74%), which is used for the next step without purification.

Workup

  1. customto give a clear solution
  2. customA condenser is attached to the RB flask
  3. customMeOH is removed
  4. dissolutionthe residue is 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 is removed in vacuo

Sources & evidence

ORD record
ord-4b1af5fab3694bc2baea7534a1cbfba6
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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