HCID 67099779, compound → HCID 67100171, compound

HRID 1868955Notes

Reaction equation

HRID 1868955 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([C:15]([CH:17]([C:23]([O:25]CC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>OS(O)(=O)=O>[F:8][C:7]1[C:2]([F:1])=[C:3]2[C:4]([CH:23]([OH:25])[CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:15](=[O:16])[C:9]32[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 67099779HCID 67099779, compound

Product 1

HCID 67100171HCID 67100171, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 10 mL concentrated H2SO4 stirred at 0° C. was added diethyl 2-(4-(2,3-difluorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (3.3 g, 8.6 mmol) dropwise. The mixture was stirred at 0° C. and allowed to warm to room temperature over 2 hours. The mixture was poured into 100 g crushed ice and extracted with EtOAc (3×100 mL). The combined organic layers were washed with saturated NaCl (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography (20% EtOAc/hexane) to give the title compound 0.23 g as a pale yellow solid. MS m/e: (M+H)+ 339.

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. additionThe mixture was poured into 100 g
  3. customcrushed ice
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layers were washed with saturated NaCl (20 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-47e3fa1c9074406dbc80d5fda2000d74
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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