HCID 68871843, compound → HCID 68872673, compound

HRID 2224827Notes

Reaction equation

HRID 2224827 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([C:11](=[O:23])[C:12]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][CH2:14][CH3:15])[C:6]([O:8]CC)=O)[CH3:2]>CS(O)(=O)=O>[OH:8][C:6]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:12]([CH3:22])([CH2:13][CH2:14][CH3:15])[C:11](=[O:23])[C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:24]

Participants

3

Reactant 1

HCID 68871843HCID 68871843, compound

Product 1

HCID 68872673HCID 68872673, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

2-(2-methyl-2-phenyl-pentanoyl)-malonic acid diethyl ester (2.45 g, 7.33 mmol) was stirred in methanesulfonic acid (20 mL) at 25° C. for 3 hours. The solution was partitioned cold water and ethyl acetate and the aqueous phase was extracted three times with ethyl acetate. The ethyl acetate layers were combined, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane followed by 5%, 10%, and 20% ethyl acetate in hexane to give the title compound (1.34 g, 63%). 1H NMR (300 MHz, CDCl3) δ ppm 0.72 (m, 4 H) 0.96 (m, 1 H) 1.46 (m, 3 H) 1.63 (s, 3 H) 1.74 (m, 0.5 H) 1.92 (m, 0.5 H) 2.26 (m, 1 H) 4.47 (m, 2 H) 7.42 (m, 2 H) 7.59 (m, 1 H) 8.16 (m, 0.5 H) 8.23 (m, 0.5 H) 15.10 (s, 0.5 H) 15.16 (s, 0.5 H). (ESI+) m/z 289 (M+H)+.

Workup

  1. customThe solution was partitioned cold water and ethyl acetate
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with hexane

Sources & evidence

ORD record
ord-3b211079a2e34eea870be3597033eb9f
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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