1-Penten-3-one → 2-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone

HRID 7855

Reaction equation

HRID 7855 reaction equation
[CH2:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[Cl:14])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].[CH:18]([C:20]([CH2:22][CH3:23])=[O:21])=[CH2:19].N12CCCN=C1CCCCC2>O1CCCC1.CCOC(C)=O>[CH2:1]([C:5]1([CH2:19][CH2:18][C:20](=[O:21])[CH2:22][CH3:23])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[Cl:14])[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 153941-Penten-3-oneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 219909172-Butyl-4-chloro-5-methoxy-1-indanone

Product 1

HCID 219909112-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanoneYield 93.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2-butyl-4-chloro-5-methoxy-1-indanone (200 mg, 0.79 mmol) in anhydrous tetrahydrofuran (0.8 mL) was placed under a nitrogen atmosphere and treated with ethyl vinyl ketone (0.118 mL, 1.19 mmol) followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (0.024 mL, 0.158 mmol). The resulting solution was stirred and heated in an oil bath at 60° C. for 47 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (20 mL) and washed with water (20 mL) containing 2N HCl (2 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to provide crude 2-butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone (250 mg) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (20 mL)
  3. additioncontaining 2N HCl (2 mL)
  4. washThe organic phase was washed with brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-d1cb4b3435da4997860140228da64a57
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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