Sulfuric Acid → HCID 67100083, compound

HRID 1868740Notes

Reaction equation

HRID 1868740 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14]([CH:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19]CC)=O)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:17]([OH:19])=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:14](=[O:15])[C:8]32[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 67100039HCID 67100039, compound

Product 1

HCID 67100083HCID 67100083, compoundYield 52.7%

Procedure

Diethyl 2-(4-(3-chlorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (10.66 g, 27.8 mmol) was added to H2SO4 (50 mL, 591 mmol), and the mixture was stirred at room temperature for 1 hour. Ice (H2O) was added, and the aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude compound as an orange oil. The crude oil was purified by silica flash chromatography (0-100% DCM/hexane) to give the desired compound as a yellow solid (4.93 g). MS (m/e)=337.1 (M+H)+.

Workup

  1. additionIce (H2O) was added
  2. extractionthe aqueous mixture was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with water (2×) and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude compound as an orange oil
  7. customThe crude oil was purified by silica flash chromatography (0-100% DCM/hexane)

Sources & evidence

ORD record
ord-e99b2fdff7cd4c93883848a80011d6b9
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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