Sulfuric Acid → HCID 67099917, compound

HRID 1868886Notes

Reaction equation

HRID 1868886 reaction equation
[C:1]1([C:7]2([C:13]([CH:15]([C:21](OCC)=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.OS(O)(=O)=O>CCOC(C)=O>[OH:22][C:21]1[C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:7]2([CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:13](=[O:14])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67099636HCID 67099636, compound

Product 1

HCID 67099917HCID 67099917, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Diethyl 2-(4-phenyl-tetrahydro-2H-pyran-4-carbonyl)malonate (418 mg, 1200 μmol) was dissolved in a minimal amount of EtOAc and then cooled to 0° C. A slurry of P2O5 (681 mg) and H2SO4 (640 μL, 11998 μmol) (also at 0° C.) was added to the mixture via spatula, and the reaction mixture was stirred for 3 hours. The reaction mixture was then poured into a beaker of ice, diluted with 100 mL of EtOAc, added to a separatory funnel, partitioned with water, washed with water (2×50 mL), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound which was used without further purification. MS m/e=303 (M+H)+.

Workup

  1. additionThe reaction mixture was then poured into a beaker of ice
  2. additionadded to a separatory funnel
  3. custompartitioned with water
  4. washwashed with water (2×50 mL)
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27179d759e92411e8810f5f49592d108
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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