Sulfuric Acid → HCID 67099777, compound
Reaction equation
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:33]([CH:35]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:36](OCC)=[O:37])=[O:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1>>[Cl:20][C:21]1[CH:22]=[C:23]2[C:24](=[CH:25][CH:26]=1)[C:27]1([CH2:28][CH2:29][O:30][CH2:31][CH2:32]1)[C:33](=[O:34])[C:35]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:36]2[OH:37]Participants
4
Procedure
Concentrated H2SO4 (9.5 mL, 18.0M) was treated with P2O5 (4.25 g, 29.9 mmol). The resulting slurry was stirred at room temperature for 2 hours. The mixture was cooled in an ice bath and treated with a solution of diethyl 2-(4-(4-chlorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (1.70 g, 4.44 mmol) in IPAc (3.0 mL). The resulting green solution was aged for 15 minutes and subsequently poured into ice water. The resulting mixture was extracted with IPAc (3×20 mL), and the combined organic extracts were dried (MgSO4). The organic solution was concentrated in vacuo to furnish a brown solid. The crude product was recrystallized from hot heptane to give the title compound as a pale yellow solid (0.81 g). MS m/e=337.2 (M+H)+.
Workup
- temperatureThe mixture was cooled in an ice bath
- waitThe resulting green solution was aged for 15 minutes
- extractionThe resulting mixture was extracted with IPAc (3×20 mL)
- dry with materialthe combined organic extracts were dried (MgSO4)
- concentrationThe organic solution was concentrated in vacuo
- customto furnish a brown solid
- customThe crude product was recrystallized from hot heptane
Sources & evidence
- ORD record
- ord-c64c2bb1ce8046c4a70352498b32d955
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928139B2
Reaction notes
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