Sulfuric Acid → HCID 67099633, compound

HRID 1868698Notes

Reaction equation

HRID 1868698 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]([CH3:42])([CH3:41])[C:28]([CH:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:31]([O:33]CC)=O)=[O:29]>>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:22]=1[C:27]([CH3:42])([CH3:41])[C:28](=[O:29])[C:30]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:31]2[OH:33]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67099240HCID 67099240, compound

Product 1

HCID 67099633HCID 67099633, compound

Procedure

A flask containing H2SO4 (12 mL, 219 mmol) and P2O5 (12 g, 88 mmol) was cooled in an ice-water bath for 20 minutes. To this viscous mixture was slowly added diethyl 2-(2-(2-fluorophenyl)-2-methylpropanoyl)malonate (7.1 g, 22 mmol). The ice bath was removed, and the mixture was stirred at room temperature for 1 hour before being poured over crushed ice and diluted with IPAc (100 mL). Water (50 mL) was added, and the resulting mixture was extracted with EtOAc (2×100 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to afford a yellow oil that was further purified using flash chromatography (10% EtOAc/hexane, 2.5 g). MS (m/z)=279 (M+H)+.

Workup

  1. temperaturewas cooled in an ice-water bath for 20 minutes
  2. customThe ice bath was removed
  3. additionbefore being poured
  4. customover crushed ice
  5. additiondiluted with IPAc (100 mL)
  6. additionWater (50 mL) was added
  7. extractionthe resulting mixture was extracted with EtOAc (2×100 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto afford a yellow oil that
  12. customwas further purified

Sources & evidence

ORD record
ord-626b5d3c410f426493e73c83db5f3b10
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

Loading…