Hydrochloric Acid → HCID 11229708, compound

HRID 1241875Notes

Reaction equation

HRID 1241875 reaction equation
C(OC([C:6]([C:20]([O:22]CC)=[O:21])([CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[CH2:7][C:8]([OH:10])=O)=O)C.C(Cl)(=O)C(Cl)=O.O.Cl>C(Cl)Cl>[CH3:19][C:14]1[C:13]2[CH2:12][CH2:11][CH:6]([C:20]([OH:22])=[O:21])[CH2:7][C:8](=[O:10])[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 65578Oxalyl chlorideHCID 21936937HCID 21936937, compound

Product 1

HCID 11229708HCID 11229708, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

16.8 g (0.0499 mol) of 3,3-bis-ethoxycarbonyl-5-o-tolyl-pentanoic acid were dissolved in 120 mL of CH2Cl2 under a nitrogen atmosphere. The solution was cooled to 5° C. and 19 mL (0.1498 mol) of oxalyl chloride were added dropwise. After 3 h the volatiles were removed in vacuo, the resulting oil was dissolved in 200 mL of CH2Cl2 and this solution was added dropwise, at 0° C. and under inert atmosphere, to a suspension of 26.6 g (0.1996 mol) of AlC3 in 300 mL of CH2Cl2. The resulting suspension was vigorously stirred overnight, during which time it was allowed to warm to room temperature. Water was added, followed by 1N HCl up to pH 1. The layers were separated, the organic phase was dried and the solvent was removed in vacuo. The resulting crude product was taken up in dioxane (60 mL) and 6N HCl (200 mL) and heated to reflux for 6 h. After cooling, water was added and the reaction mixture was extracted with Et2O. The organic phase was dried, the solvent was removed in vacuo and the resulting crude product was purified by flash chromatography eluting with Et2O, yielding 5.9 g of compound which was triturated in (i-Pr)2O, filtered and dried, yielding 4.33 g of the title product.

Workup

  1. customAfter 3 h the volatiles were removed in vacuo
  2. dissolutionthe resulting oil was dissolved in 200 mL of CH2Cl2
  3. temperatureto warm to room temperature
  4. customThe layers were separated
  5. customthe organic phase was dried
  6. customthe solvent was removed in vacuo
  7. temperature6N HCl (200 mL) and heated
  8. temperatureto reflux for 6 h
  9. temperatureAfter cooling
  10. additionwater was added
  11. extractionthe reaction mixture was extracted with Et2O
  12. customThe organic phase was dried
  13. customthe solvent was removed in vacuo
  14. customthe resulting crude product was purified by flash chromatography
  15. washeluting with Et2O

Sources & evidence

ORD record
ord-1565f390a0d44d5d9bda9d6be3141479
Source dataset
uspto-grants-2006_10
Patent number
US07115633B2

Reaction notes

Loading…