Tetrahydrofuran → HCID 16639026, compound

HRID 422220Notes

Reaction equation

HRID 422220 reaction equation
[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.CO[C:10](=[O:13])[O:11][CH3:12].COC1C=[C:18]2[C:22](=[CH:23]C=1)[C:21](=[O:25])[CH2:20][CH2:19]2>C(OCC)(=O)C>[CH3:12][O:11][C:10]([CH:20]1[CH2:19][C:18]2[C:22](=[CH:23][C:7]([O:6][CH3:5])=[CH:3][CH:4]=2)[C:21]1=[O:25])=[O:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 787875-Methoxyindan-1-one

Product 1

HCID 16639026HCID 16639026, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine NaH (5.4 g, 122.1 mmol), THF anhydrous (150 mL), and dimethylcarbonate (6.6 mL, 81.3 mmol). While refluxing the reaction under a nitrogen atmosphere, add dropwise 5-Methoxyindanone (3.46 g, 21.33 mmol) over one hour. After the reaction mixture refluxes for 12 hours, quench using Acetic acid and then add Ethyl acetate to the reaction mixture in a separatory funnel. Wash the organic layer several times with water and dry the organic layer over Na2SO4 followed by concentration under reduced pressure. Flash Chromatograph using 1:1 Hexanes:Ethyl acetate to afford 3.14 g, 14.3 mmol (67% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 3.3-3.4 (1H, dd), 3.5-3.6 (1H, dd), 3.7-3.8 (1H, m), 3.8 (3H, s), 3.9 (3H, s), 6.8-7.0 (2H, m), 7.7-7.8 (1H, m); TLC 2:1 Hexanes:Ethyl acetate Rf:=0.4.

Workup

  1. temperatureWhile refluxing
  2. customthe reaction under a nitrogen atmosphere
  3. customquench
  4. washWash the organic layer several times with water
  5. dry with materialdry the organic layer over Na2SO4
  6. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-1870dd6ffe18498e8d433cfa703e1744
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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