Sulfuric Acid → HCID 67099309, compound
Reaction equation
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Br:20][C:21]1[CH:22]=[C:23]([C:29]2([C:35]([CH:37]([C:43](OCC)=[O:44])[C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>CCOC(C)=O>[Br:20][C:21]1[CH:22]=[C:23]2[C:24]([C:43]([OH:44])=[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:35](=[O:36])[C:29]32[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)=[CH:25][C:26]=1[O:27][CH3:28]Participants
Procedure
In a 100 mL round bottom flask, 5 mL concentrated H2SO4 stirred at 0° C. was carefully treated with 2.5 g P2O5. The resulting mixture was stirred for 10 minutes. A mixture of diethyl 2-(4-(3-bromo-4-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (1.25 g, 2.7 mmol) in 2 mL EtOAc was added to the above H2SO4 mixture, and the mixture was stirred at room temperature for 2 hours, M+1=411/413. The reaction mixture was then poured into 200 g crushed ice. The mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-50% EtOAc/hexane to give 0.28 g of the product as a pale yellow solid. MS m/e=411/413 (M+H)+.
Workup
- stirringthe mixture was stirred at room temperature for 2 hours
- additionThe reaction mixture was then poured into 200 g
- customcrushed ice
- extractionThe mixture was extracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with brine (20 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- custompurified by column chromatography
- washeluting with 10-50% EtOAc/hexane
Sources & evidence
- ORD record
- ord-4613d5a1149f474894fabc9708f5ef7e
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928139B2
Reaction notes
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