HCID 67099404, compound → HCID 67099458, compound

HRID 1868662Notes

Reaction equation

HRID 1868662 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([CH:17]([C:23](OCC)=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1>OS(O)(=O)=O>[OH:24][C:23]1[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[C:9]2([CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:15](=[O:16])[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

3

Reactant 1

HCID 67099404HCID 67099404, compound

Product 1

HCID 67099458HCID 67099458, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Diethyl 2-(4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (2.2 g) in 1 mL IPAc was added to 20 mL of concentrated H2SO4, and the resulting mixture was stirred at room temperature for 2 hours, M+1=333, M−1=331. The mixture was then poured into 200 g of 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 0.66 g of the title product as a yellow oil. MS (m/z)=333 (M+H)+.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography
  6. washeluting with 10-50% EtOAc/hexane

Sources & evidence

ORD record
ord-8835d0d02d5042c8aeb9116e220373db
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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