Potassium Carbonate → 2-[4-(3-Chloro-2-methylpropoxy)phenyl]-3-oxa-1-azaspiro[4.5]dec-1-ene

HRID 251465Notes

Reaction equation

HRID 251465 reaction equation
[N:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][O:3][C:2]=1[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.Br[CH2:19][CH:20]([CH3:23])[CH2:21][Cl:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:22][CH2:21][CH:20]([CH3:23])[CH2:19][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:2]2[O:3][CH2:4][C:5]3([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]3)[N:1]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 955661-Bromo-3-chloro-2-methylpropaneHCID 1355265344-(3-Oxa-1-azaspiro[4.5]dec-1-en-2-yl)phenol

Product 1

HCID 119509122-[4-(3-Chloro-2-methylpropoxy)phenyl]-3-oxa-1-azaspiro[4.5]dec-1-eneYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(3-oxa-1-azaspiro[4.5]dec-1-en-2-yl)phenol ax8 (0.5 g, 2.16 mmol, 1 eq) in acetone (30 ml) is added 1-bromo-3-chloro-2-methylpropane (0.25 ml, 2.16 mmol, 1 eq) and potassium carbonate (0.6 g, 4.32 mmol, 2 eq). The mixture is stirred at reflux for 13 days. The mixture is concentrated, taken up in dichloromethane and washed twice with a saturated aqueous solution of ammonium chloride. The organic layer is dried over magnesium sulfate and the solvent is removed under reduced pressure to afford 0.7 g of 2-[4-(3-chloro-2-methylpropoxy)phenyl]-3-oxa-1-azaspiro[4.5]dec-1-ene ax64 as a colorless oil. This crude product is used in the next step without further purification.

Workup

  1. temperatureat reflux for 13 days
  2. concentrationThe mixture is concentrated
  3. washwashed twice with a saturated aqueous solution of ammonium chloride
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-92e8e93ab0034f668ea2f096302813fb
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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