Hydrochloric Acid → HCID 20281915, compound

HRID 463048Notes

Reaction equation

HRID 463048 reaction equation
C(NC(C)C)(C)C.[C:8]1([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:20]([O:23][CH:24](C)[CH2:25][CH2:26][CH2:27]I)(=[O:22])[CH3:21].Cl>O1CCCC1>[C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7590Ethyl phenylacetateHCID 7912DiisopropylamineHCID 117472172-Pentanol, 5-iodo-, 2-acetate

Product 1

HCID 20281915HCID 20281915, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

Diisopropylamine (2.4 g, 23.8 mmole) was dissolved in anhydrous tetrahydrofuran (50 ml) under argon, and the solution was cooled at -70° C. 1.6M n-butyllithium-hexane solution (14.8 ml, 23.7 mmole) was added dropwise to the solution, followed by stirring at -70° C. for 10 minutes. Tetrahydrofuran (10 ml) solution containing ethyl phenylacetate (3.24 g, 20 mmole) was added, while maintaining the reaction solution at not higher than -60° C. After stirring was continued for 30 minutes under the same conditions, a solution of 4-acetoxypentyl iodide (4.8 g, 20 mmole) in hexamethylphosphortriamide (4 ml) was added dropwise to the reaction solution. Following the dropwise addition, stirring was continued at -70° C. for another 1 hour, and the reaction temperature was allowed to rise to room temperature. 2N hydrochloric acid (30 ml) was added, and the product was extracted with isopropyl ether. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on silica gel, and development was effected with isopropyl ether:hexane (1:1) to yield ethyl 6-acetoxy-2-phenylhexanoate (5 g, 90%).

Workup

  1. addition1.6M n-butyllithium-hexane solution (14.8 ml, 23.7 mmole) was added dropwise to the solution
  2. additionwas added
  3. temperaturewhile maintaining the reaction solution at not higher than -60° C
  4. stirringAfter stirring
  5. waitwas continued for 30 minutes under the same conditions
  6. additionthe dropwise addition
  7. stirringstirring
  8. waitwas continued at -70° C. for another 1 hour
  9. customto rise to room temperature
  10. extractionthe product was extracted with isopropyl ether
  11. washThe organic layer was washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was chromatographed on silica gel, and development

Sources & evidence

ORD record
ord-9d4a357de3554d6b88dc18f8cdb1337f
Source dataset
uspto-grants-1985_05
Patent number
US04518602

Reaction notes

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