Cesium carbonate → 3,3,4,4-Tetrafluoro-2,3,4,5-tetrahydro-1,6-benzodioxocine-8-carbaldehyde
Reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].FC(F)(F)S(O[CH2:17][C:18]([F:32])([F:31])[C:19]([F:30])([F:29])[CH2:20][O:21]S(C(F)(F)F)(=O)=O)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:29][C:19]1([F:30])[CH2:20][O:21][C:9]2[CH:2]=[CH:3][C:4]([CH:5]=[O:6])=[CH:7][C:8]=2[O:10][CH2:17][C:18]1([F:32])[F:31]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 2 g of 3,5-dihydroxybenzaldehyde, 10 g of 2,2,3,3-tetrafluorobutane-1,4-diyl bis(trifluoromethanesulfonate) and 12 g of cesium carbonate in 100 mL of anhydrous acetonitrile was heated under nitrogen to 50° C. overnight. The mixture was allowed to cool, then filtered and concentrated under reduced pressure. The residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate then dried over magnesium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-35% ethyl acetate in hexanes) gave the product as crystalline solid. MS (m+1)=265.1; 1H NMR (400 MHz, CDCl3) 9.85 (s, 1H), 7.6 (m, 2H), 7.2 (d, 1H), 4.64 (t, 2H), 4.45 (t, 2H).
Workup
- temperatureto cool
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was partitioned between 250 mL of ethyl acetate and 100 mL of saturated sodium carbonate
- dry with materialthen dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customPurification by flash chromatography (0-35% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-64d15b8f533048edae3baf750ff9c5ac
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855201B2
Reaction notes
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