Sulfuric Acid → HCID 67099306, compound

HRID 2078140Notes

Reaction equation

HRID 2078140 reaction equation
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[F:20][C:21]1[CH:22]=[C:23]([C:27]2([C:33]([CH:35]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:36]([O:38]CC)=O)=[O:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[CH:24]=[CH:25][CH:26]=1>>[F:20][C:21]1[CH:22]=[C:23]2[C:24]([C:36]([OH:38])=[C:35]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:33](=[O:34])[C:27]32[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14812Phosphorus oxide (P4O10)HCID 670994421,3-Diethyl 2-[[4-(3-fluorophenyl)tetrahydro-2H-pyran-4-yl]carbonyl]propanedioate

Product 1

HCID 67099306HCID 67099306, compoundYield 22.1%

Procedure

H2SO4 (25 mL, 296 mmol) was cooled to 0° C. and treated with P2O5 (10 g, 70 mmol). The mixture was brought to room temperature and was then added to diethyl 2-(4-(3-fluorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate (4.23 g, 12 mmol). The resulting reaction mixture was then stirred 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 (50-100% DCM/hexane) to give the desired compound as a white solid (850 mg). MS (m/e)=321.1 (M+H)+.

Workup

  1. customwas brought to room temperature
  2. customThe resulting reaction mixture
  3. additionIce (H2O) was added
  4. extractionthe aqueous mixture was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with water (2×) and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give the crude compound as an orange oil
  9. customThe crude oil was purified by silica flash chromatography (50-100% DCM/hexane)

Sources & evidence

ORD record
ord-08c155d30a3141de8e1e1ce6d52c535c
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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