Sulfuric Acid → HCID 67099697, compound

HRID 1868789Notes

Reaction equation

HRID 1868789 reaction equation
OS(O)(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2([C:20]([CH:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23](OCC)=[O:24])=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:10]=[CH:11][C:12]=1[Cl:13]>CCOC(C)=O>[Cl:13][C:12]1[CH:11]=[C:10]2[C:9](=[CH:8][C:7]=1[Cl:6])[C:14]1([CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:20](=[O:21])[C:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:23]2[OH:24]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67100085HCID 67100085, compound

Product 1

HCID 67099697HCID 67099697, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Concentrated H2SO4 (4203 μL) was added to solid diethyl 2-(4-(3,4-dichlorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (3.29 g, 7884 μmol) at ambient temperature. The reaction was heated at 50° C. for 6 hours and then poured into a flask of ice, diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with water, washed 2 times with 50 mL of water, separated, dried over Na2SO4, and concentrated in vacuo to give the purified title compound (375 mg) after flash chromatography as a pale yellow solid. MS (m/z)=371 (M+H)+.

Workup

  1. additionpoured into a flask of ice
  2. additionadded to a separatory funnel
  3. custompartitioned with water
  4. washwashed 2 times with 50 mL of water
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give the
  9. custompurified title compound (375 mg) after flash chromatography as a pale yellow solid

Sources & evidence

ORD record
ord-d981108053144d9983002b6750298fc7
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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