Sulfuric Acid → HCID 67099747, compound
Reaction equation
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:20][C:21]([F:48])([F:47])[C:22]1[CH:23]=[C:24]([C:28]2([C:34]([CH:36]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:37](OCC)=[O:38])=[O:35])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1>>[F:20][C:21]([F:47])([F:48])[C:22]1[CH:23]=[C:24]2[C:25]([C:37]([OH:38])=[C:36]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:34](=[O:35])[C:28]32[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:26][CH:27]=1Participants
4
Procedure
H2SO4 (25 mL, 296 mmol) was cooled to 0° C. and treated with P2O5 (10 g, 70 mmol). The mixture was brought to room temperature and added to diethyl 2-(4-(3-(trifluoromethyl)phenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (4.27 g, 10 mmol). The reaction mixture was then stirred for 1.5 hours. Ice (H2O) was added, and the aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude compound as a brown oil. The crude oil was purified by silica flash chromatography (0-100% DCM/hexane) to give the desired compound as a white solid (1.32 g). MS (m/e)=371.2 (M+H)+.
Workup
- customwas brought to room temperature
- additionIce (H2O) was added
- extractionthe aqueous mixture was extracted with EtOAc (2×)
- washThe combined organic layers were washed with water (2×) and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give the crude compound as a brown oil
- customThe crude oil was purified by silica flash chromatography (0-100% DCM/hexane)
Sources & evidence
- ORD record
- ord-31ad4d01c3e1465786df273cd5cbee42
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928139B2
Reaction notes
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