Sodium Acetate → HCID 278205, compound

HRID 2202732Notes

Reaction equation

HRID 2202732 reaction equation
N1([C:6]2[CH2:14][CH2:13][C:12]3([C:15]([O:17][CH3:18])=[O:16])[C:8](=[CH:9][CH2:10][CH2:11]3)[CH:7]=2)CCCC1.C([O-])(=[O:21])C.[Na+]>C1(C)C=CC=CC=1.CC(O)=O.O.CCOC(C)=O>[O:21]=[C:6]1[CH:7]=[C:8]2[C:12]([C:15]([O:17][CH3:18])=[O:16])([CH2:11][CH2:10][CH2:9]2)[CH2:13][CH2:14]1

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 118342996HCID 118342996, compound

Product 1

HCID 278205HCID 278205, compoundYield 48.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

The crude enamine from Step 2 was dissolved in toluene (20 mL) and a solution of sodium acetate (1.360 ml, 25.3 mmol) in AcOH/water (4/4 mL) was added and the resulting mixture was heated to reflux under N2 atmosphere for 2 h. The reaction went to completion, diluted with EtOAc, washed with water, sat. NH4Cl, sat. NaHCO3, brine, dried over Na2SO4, filtered, concentrated and chromatographed on silica gel using 0-30% heptane/EtOAc to afford methyl 6-oxo-2,3,3a,4,5,6-hexahydro-1H-indene-3a-carboxylate (1.32 g, 6.80 mmol, 48.3% yield) as a bright yellow oil. MS m/z=195.2 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under N2 atmosphere for 2 h
  3. washwashed with water, sat. NH4Cl, sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel using 0-30% heptane/EtOAc

Sources & evidence

ORD record
ord-0be028c6b1864144be75fc6b0b29567b
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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