Hydrochloric Acid → 2-[2-(2-Ethyl-[1,3]dioxolan-2-yl)-ethyl]-5-methoxy-3-propyl-1-indanone

HRID 7877

Reaction equation

HRID 7877 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH:6]2[CH2:13][CH2:14][CH3:15].[CH2:16]([C:18]1([CH2:23][CH:24]=O)[O:22][CH2:21][CH2:20][O:19]1)[CH3:17].[OH-].[K+].Cl>C(O)C.[Pd]>[CH2:16]([C:18]1([CH2:23][CH2:24][CH:7]2[CH:6]([CH2:13][CH2:14][CH3:15])[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:8]2=[O:12])[O:22][CH2:21][CH2:20][O:19]1)[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 134892232-(2-Ethyl-1,3-dioxolan-2-yl)acetaldehydeHCID 219908595-Methoxy-3-propyl-1-indanone

Product 1

HCID 219908532-[2-(2-Ethyl-[1,3]dioxolan-2-yl)-ethyl]-5-methoxy-3-propyl-1-indanoneYield 29.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-methoxy-3-propyl-1-indanone (184 mg, 0.90 mmol) and (2-ethyl-[1,3]dioxolan-2-yl)acetaldehyde (173 mg, 1.20 mmol) was treated with a solution of KOH (85% wt. pure, 20 mg, 0.30 mmol) in ethanol (1.0 mL). The resulting mixture was stirred at room temperature for 30 minutes, then treated with 10% Pd on carbon (9 mg), placed under a hydrogen atmosphere, and stirred vigorously at room temperature for 18 hours. The mixture was acidified with 2N HCl and partitioned between EtOAc (9 mL) and water (5 mL). The organic phase was washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to an oil (316 mg). The crude product was purified by chromatography on a Biotage FLASH 12M column, eluting with 10% EtOAc in hexanes, to afford 2-[2-(2-ethyl-[1,3]dioxolan-2-yl)-ethyl]-5-methoxy-3-propyl-1-indanone (87 mg) as an oil.

Workup

  1. stirringstirred vigorously at room temperature for 18 hours
  2. custompartitioned between EtOAc (9 mL) and water (5 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to an oil (316 mg)
  7. customThe crude product was purified by chromatography on a Biotage FLASH 12M column
  8. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-61d811177b4e4cd88b1e29266c8ae876
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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