Acetic Acid → 6-Chloro-9a-(2-fluoroethyl)-7-methoxy-9,9a-dihydro-1H-fluoren-3(2H)-one

HRID 1788095Notes

Reaction equation

HRID 1788095 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]([CH2:17][CH2:18][F:19])([CH2:12][CH2:13][C:14](=[O:16])[CH3:15])[C:8]2=O)=[CH:4][C:3]=1[O:20][CH3:21].C(O)(=O)C.N1CCCC1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:20][CH3:21])[CH2:6][C:7]1([CH2:17][CH2:18][F:19])[C:8]2=[CH:15][C:14](=[O:16])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 57603342HCID 57603342, compound

Product 1

HCID 534381796-Chloro-9a-(2-fluoroethyl)-7-methoxy-9,9a-dihydro-1H-fluoren-3(2H)-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 6-chloro-2-(2-fluoroethyl)-5-methoxy-2-(3-oxobutyl)indan-1-one (32 g, 102 mmol) in toluene (1000 mL) were added acetic acid (7.0 mL, 120 mmol) and pyrrolidine (10 mL, 120 mmol) and the solution was heated at 95° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (1000 mL), washed with water and saturated aqueous NaHCO3, and dried over MgSO4. Filtration through a pad of silica gel and removal of the solvent under vacuum gave 6-chloro-9a-(2-fluoroethyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and saturated aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationFiltration
  5. customthrough a pad of silica gel and removal of the solvent under vacuum

Sources & evidence

ORD record
ord-6fc3ff70fc1145e6965aa98f5831f3c5
Source dataset
uspto-grants-2009_03
Patent number
US07511152B2

Reaction notes

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