HCID 18624145, compound → HCID 18624173, compound

HRID 1860637Notes

Reaction equation

HRID 1860637 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([CH3:22])([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl.O1CCO[CH2:26][CH2:25]1>CCO>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([CH3:21])([CH3:22])[CH2:17][C:18]([O:20][CH2:25][CH3:26])=[O:19])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 18624145HCID 18624145, compoundHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 18624173HCID 18624173, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The acid from STEP 3 (0.5 g) was suspended in absolute EtOH (3.0 mL), added 4N HCl/dioxane (2.0 mL) and stirred overnight at room temperature, and heated to reflux for 1 h. The solution was concentrated to dryness and the residue was dissolved in EtOAC (15 mL), washed with water, dried and concentrated to dryness. The resulting syrup (0.4 g) was dissolved in EtOH (10 mL), added acetic acid (0.1 mL), Pd/C (10%, 0.25 g), and stirred in an atmosphere of hydrogen gas at 50 psi at room temperature. After 16 h, the catalyst was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure. The resulting colorless syrup was dried in vacuo to give the title compound (0.34 g, 80%): Rf=0.44 (50% EtOAc/Hexane); 1H -NMR (CDCl3) δ7.02 (d, 2H); 6.73 (d, 2H); 4.12 (q, 2H); 2.58 (s, 2H); 2.15 (d, 2H); 1.24 (t, 3H); 0.98 (s, 6H); ES-MS m/z 235(M-H); HRMS calcd C14H21O3 (MH+) 237.1485, found 237.1511.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. concentrationThe solution was concentrated to dryness
  4. dissolutionthe residue was dissolved in EtOAC (15 mL)
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated to dryness
  8. dissolutionThe resulting syrup (0.4 g) was dissolved in EtOH (10 mL)
  9. additionadded acetic acid (0.1 mL), Pd/C (10%, 0.25 g)
  10. stirringstirred in an atmosphere of hydrogen gas at 50 psi at room temperature
  11. waitAfter 16 h
  12. customthe catalyst was removed by filtration
  13. concentrationthe filtrate was concentrated to dryness under reduced pressure
  14. customThe resulting colorless syrup was dried in vacuo

Sources & evidence

ORD record
ord-fb8de788e7c746ea9721fb3debbd7ecf
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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