Sulfuric Acid → HCID 67099732, compound
Reaction equation
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1([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]1>CCOC(C)=O.CCCCCC>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:22]=1[C:27]1([CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[C:33](=[O:34])[C:35]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:36]2[OH:37]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A flask containing H2SO4 (12 mL, 218 mmol) and P2O5 (12 g, 87 mmol) was cooled in an ice bath for 20 minutes under nitrogen, and then diethyl 2-(4-(2-fluorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (8.0 g, 22 mmol) was added dropwise over 10 minutes. The reaction was stirred an additional 10 minutes at 0° C., and then was stirred at room temperature for 1 hour. The reaction was poured over ice and allowed to melt. The aqueous mixture was extracted with EtOAc (3×100 mL) and then the separated organic extracts were dried (Na2SO4), filtered and concentrated to provide an oil. Flash chromatography (20% EtOAc/hexane) afforded an oil (3.6 g). MS m/e=321.0 (M+H)+.
Workup
- temperaturewas cooled in an ice bath for 20 minutes under nitrogen
- stirringwas stirred at room temperature for 1 hour
- additionThe reaction was poured over ice
- extractionThe aqueous mixture was extracted with EtOAc (3×100 mL)
- dry with materialthe separated organic extracts were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customto provide an oil
Sources & evidence
- ORD record
- ord-7972b49c34df422d8b920a4eb5f4a91a
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635715B2
Reaction notes
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