Sulfuric Acid → HCID 67099891, compound

HRID 1868644Notes

Reaction equation

HRID 1868644 reaction equation
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:32]([CH:34]([C:40](OCC)=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:33])[CH2:31][CH2:30][O:29][CH2:28]2)=[CH:23][CH:22]=1>CCOC(C)=O>[Cl:20][C:21]1[CH:26]=[C:25]2[C:24](=[CH:23][CH:22]=1)[C:27]1([CH2:31][CH2:30][O:29][CH2:28]1)[C:32](=[O:33])[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:40]2[OH:41]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 67099687HCID 67099687, compound

Product 1

HCID 67099891HCID 67099891, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Concentrated H2SO4 (66483 mg, 677858 μmol) was cooled to 0° C. and treated with P2O5 (11546 mg, 81343 μmol). The reaction was stirred for 60 minutes and treated with diethyl 2-(3-(4-chlorophenyl)-tetrahydrofuran-3-carbonyl)malonate (5 g, 13557 μmol). After 60 minutes, the reaction was diluted with EtOAc and poured onto ice. The aqueous layer was extracted with EtOAc (3×), and the combined organic layers were washed with brine and dried over MgSO4. Purification by silica flash chromatography (2-5% MeOH/DCM) gave the title compound as a white solid. MS m/e=323.2 (M+H)+.

Workup

  1. waitAfter 60 minutes
  2. additionpoured onto ice
  3. extractionThe aqueous layer was extracted with EtOAc (3×)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customPurification by silica flash chromatography (2-5% MeOH/DCM)

Sources & evidence

ORD record
ord-55ff3c1a1bc24648b885af619475290c
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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