Hydrochloric Acid → HCID 53663024, compound

HRID 1995273Notes

Reaction equation

HRID 1995273 reaction equation
C(NC1CCCCC1)(C)C.C([Li])CCC.[C:16]([O:19][CH2:20][CH3:21])(=[O:18])[CH3:17].[CH2:22]([O:24][CH:25]([O:47][CH2:48][CH3:49])[CH2:26][C:27](=[O:46])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH2:38][CH:39]=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH3:23].Cl>O1CCCC1>[CH2:48]([O:47][CH:25]([O:24][CH2:22][CH3:23])[CH2:26][C:27]([OH:46])([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH2:38][CH:39]=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:17][C:16]([O:19][CH2:20][CH3:21])=[O:18])[CH3:49]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 62386CyclohexylisopropylamineHCID 53826091HCID 53826091, compoundHCID 178418339Butyllithium

Product 1

HCID 53663024HCID 53663024, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

Isopropyl cyclohexylamine (565 mg, 4 mmole) in 10 ml of anhydrous tetrahydrofuran was cooled to -78° C. in a 3 neck round bottom flask and n-butyl lithium (2 ml, 4 mmole) was added dropwise. After 10 minutes, ethyl acetate (300 mg, 4 mmole) in 5 ml of tetrahydrofuran was added dropwise over a 15 minute period and the reaction mixture was stirred for 30 minutes at -78° C. following the addition. 1,1-Diethoxy-12,15-heneicosadiene-3-one (1.5 g) in 5 ml of tetrahydrofuran was added within 1 minute and the mixture was maintained at -78° C. for another 30 minutes. 5% Aqueous hydrochloric acid (5 ml) was added and the mixture was warmed to room temperature. Solvent was removed in vacuo and 40 ml of pentane was added. The organic layer was washed until neutral and was dried, worked up to provide 1.0 g of crude reaction mixture. After purification from column chromatography, the desired product was obtained as heavy oil (1.4 g) of formula XI of Chart B.

Workup

  1. additionwas added dropwise
  2. additionthe addition
  3. temperaturethe mixture was maintained at -78° C. for another 30 minutes
  4. temperaturethe mixture was warmed to room temperature
  5. customSolvent was removed in vacuo and 40 ml of pentane
  6. additionwas added
  7. washThe organic layer was washed until neutral and
  8. customwas dried
  9. customto provide 1.0 g of crude
  10. customreaction mixture
  11. customAfter purification from column chromatography

Sources & evidence

ORD record
ord-93a5d83cdbdb45838aaad4e9d313f63a
Source dataset
uspto-grants-1983_09
Patent number
US04404144

Reaction notes

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