Hydrochloric Acid → HCID 58075770, compound

HRID 2370230Notes

Reaction equation

HRID 2370230 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].[C:15](=O)([O:18]C)[O:16][CH3:17].[H-].[Na+].Cl>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH:11]([C:15]([O:16][CH3:17])=[O:18])[C:10]1=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 123337222-(2-Methoxyphenyl)cyclopentan-1-one

Product 1

HCID 58075770HCID 58075770, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Procedure

A mixture of 2-(2-methoxyphenyl)cyclopentanone (6.64 g, 34.9 mmol), dimethyl carbonate (58.8 ml, 698 mmol) and MeOH (4 drops) was stirred while sodium hydride (3.07 g, 60% wt, 77 mmol) was added slowly at 0° C. The mixture was warmed to RT and then heated to reflux for 2 hr and then stirred at RT overnight. The reaction was quenched with 1 N HCl (77 mL, 77 mmol) and extracted with ethyl acetate. The organic extracts were washed with water, dried with brine, and concentrated in vacuo. The crude product was purified by flash chromatography (SG, 0 to 75% EtOAc/Hexane) to get methyl 3-(2-methoxyphenyl)-2-oxocyclopentanecarboxylate (5.3 g, 21.35 mmol, 61.2% yield). LC-MS (M+Na)+=271.1. 1H NMR (500 MHz, CD3OD) δ 7.26-7.16 (m, 1H), 7.08 (d, J=7.3 Hz, 1H), 6.92-6.84 (m, 2H), 3.73-3.69 (m, 3H), 3.68 (s, 3H), 3.60-3.49 (m, 1H), 3.49-3.40 (m, 1H), 2.40-2.31 (m, 1H), 2.31-2.17 (m, 2H), 2.16-2.01 (m, 1H).

Workup

  1. addition77 mmol) was added slowly at 0° C
  2. temperatureheated
  3. temperatureto reflux for 2 hr
  4. extractionextracted with ethyl acetate
  5. washThe organic extracts were washed with water
  6. dry with materialdried with brine
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography (SG, 0 to 75% EtOAc/Hexane)

Sources & evidence

ORD record
ord-1325f893b9cd403dbbb90c3e4ceeaed1
Source dataset
uspto-grants-2014_04
Patent number
US08710061B2

Reaction notes

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