Sulfuric Acid → HCID 67099505, compound

HRID 2078077Notes

Reaction equation

HRID 2078077 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2([C:15]([CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18](OCC)=[O:19])=[O:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.OS(O)(=O)=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:18]([OH:19])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:15](=[O:16])[C:9]12[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67099313Diethyl 2-(4-(3-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate

Product 1

HCID 67099505HCID 67099505, compoundYield 2.7%

Conditions

Temperature
0 °C

Procedure

Diethyl 2-(4-(3-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (2.1 g) was added to 5 mL H2SO4 stirred at 0° C. The mixture was stirred at room temperature for 1 hour, M+1=379. The mixture was then poured into 100 g crushed ice and extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was purified by column chromatography eluting with 20% EtOAc/hexane to give 0.05 g of the title compound. MS (m/z)=379 (M+H)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. additionThe mixture was then poured into 100 g
  3. customcrushed ice
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined organic layers were washed with H2O (20 mL) and brine (20 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-85d3506b93df4a0087c3ff76cdd8d965
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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