Acetic Acid → 7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7820

Reaction equation

HRID 7820 reaction equation
N1CCCC1.C(O)(=O)C.[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=O)[C:16]([CH3:27])([CH2:22][CH2:23][C:24](=[O:26])[CH3:25])[CH2:15]2>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18]([C:17]3[C:16]([CH3:27])([CH2:15]2)[CH2:22][CH2:23][C:24](=[O:26])[CH:25]=3)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 219909085-Methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone

Product 1

HCID 219909037-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-oneYield 99.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

Pyrrolidine (0.159 mL, 1.9 mmol) and acetic acid (0.109 mL, 1.9 mmol) were added to a solution of 5-methoxy-2-methyl-2-(3-oxo-butyl)-1-indanone (467 mg, 1.9 mmol) in toluene (5 mL) and the resulting solution was heated in an oil bath at 85° C. for 2.5 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (20 mL), washed with water (20 mL), 5% NaHCO3 (20 mL), and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to yield 7-methoxy-9a-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (430 mg) as a light brown solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (20 mL), 5% NaHCO3 (20 mL), and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-d6636cf7073446fb80a814617775f2cf
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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