Water → 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1H-inden-1-one
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.O>CCCCCC>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:10](=[O:12])[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[CH2:8]2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A solution of 500 g of polyphosphoric acid was heated to 60° C. and 43.0 g of the acid from step A was added. The mixture was then heated to 110° C. for 1 hour. After this time, the reaction was cooled to about 60° C. and 400 mL of water was added rapidly with externalcooling. The mixture was then partitioned between toluene and water, washed twice with toluene and the combined toluene extracts were then washed with 5% aqueous NaHCO3. The toluene extracts were then dried over MgSO4, filtered, concentrated and chromatographed on silica gel with 10% ethyl acetate in hexane as the eluent to afford, after trituration with hexane, 26.98 g of a yellow solid; mp 72°-74° C. 1H NMR (CDCl3) δ: 3.22 (dd, 1H), 3.70 (dd, 1H), 3.94 (dd, 1H), 7.0-7.3 (m, 5H), 7.82 (dd, 1H).
Workup
- temperatureAfter this time, the reaction was cooled to about 60° C.
- customThe mixture was then partitioned between toluene and water
- washwashed twice with toluene
- washthe combined toluene extracts were then washed with 5% aqueous NaHCO3
- dry with materialThe toluene extracts were then dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica gel with 10% ethyl acetate in hexane as the eluent
- customto afford
Sources & evidence
- ORD record
- ord-2e5115cc84634afc8e69be43285a6264
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380718
Reaction notes
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