Pyridine → HCID 91204141, compound

HRID 132734Notes

Reaction equation

HRID 132734 reaction equation
[CH2:1]([C:6]([CH:11]([CH3:13])[CH3:12])([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH:3]([CH3:5])[CH3:4].N1C=CC=CC=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:29](Cl)(=[O:32])[CH2:30][CH3:31]>O.O1CCCC1>[C:29]([O:8][CH2:7][C:6]([CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])([CH:11]([CH3:13])[CH3:12])[CH2:9][O:10][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:32])[CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 7412Benzoyl chlorideHCID 62324Propionyl chlorideHCID 117453912-(3-Methylbutyl)-2-(propan-2-yl)propane-1,3-diol

Product 1

HCID 91204141HCID 91204141, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 7.5 g (0.05 mol) 2-isoamyl-2-isopropyl-1,3-propandiol, which was prepared according to the process described in synthetic example 63, was added 50 ml tetrahydrofuran, then added 4.8 ml (0.06 mol) pyridine with stirring. To the resulting homogenous mixture was slowly added 4.6 ml (0.04 mol) benzoyl chloride. The mixture was stirred at room temperature for 1 hour and heated refluxing for 5 hours. Upon completing the reaction, the reaction mixture was cooled to room temperature. To the mixture was added 30 ml tetrahydrofuran, then added 4.8 ml (0.06 mol) pyridine with stirring. To the resulting homogenous mixture was slowly added 3.5 ml (0.04 mol) propionyl chloride. The mixture was stirred at room temperature for 1 hour, and heated refluxing for 5 hours. Upon completing the reaction, 40 ml water was added to dissolve the resulting salt. The mixture was extracted with ethyl acetate. The organic phase was separated, washed with saturated saline for two times, and dried over anhydrous sodium sulfate. The solvent was removed. Distillation under reduced pressure gave colorless liquid 2-isoamyl-2-isopropyl-1,3-propandiol monobenzoate monopropionate, and the yield was 91%. 1HNMR: δ (ppm) 0.87(d, 6H, CH3 of isoamyl), 0.93(d, 6H, CH3 of isopropyl), 0.99(t, 2H, CH3 of propionyl), 1.06(m, 4H, CH2 of isoamy), 1.11(m, 1H, CH of isoamyl), 1.14(m, 1H, CH of isopropyl), 2.29(m, 2H, CH2O of 1,3-propandiol), 4.28(m, 2H, CH2O of 1,3-propandiol), 4.38 (m, 2H, CH2 of propionyl), 7.41-8.03(m, 5H, ArH)

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 5 hours
  4. customthe reaction
  5. stirringwith stirring
  6. stirringThe mixture was stirred at room temperature for 1 hour
  7. temperatureheated
  8. temperaturerefluxing for 5 hours
  9. additionwas added
  10. dissolutionto dissolve the resulting salt
  11. extractionThe mixture was extracted with ethyl acetate
  12. customThe organic phase was separated
  13. washwashed with saturated saline for two times
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe solvent was removed
  16. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-14f0c9d6de2c4e41803b2bc90e3ae729
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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