Pyridine → HCID 91170071, compound

HRID 132735Notes

Reaction equation

HRID 132735 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].[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.N1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25](Cl)(=[O:34])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[C:18]([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:25](=[O:34])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:14])[CH:17]=[CH:16][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 660233-Phenylprop-2-enoyl chlorideHCID 117453912-(3-Methylbutyl)-2-(propan-2-yl)propane-1,3-diol

Product 1

HCID 91170071HCID 91170071, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7.5 g (0.04 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 9.7 ml (0.12 mol) pyridine with stirring. To the resulting homogenous mixture was slowly added 16.7 g(0.1 mol) cinnamoyl chloride. The mixture was stirred at room temperature for 1 hour, and heated refluxing for 4 hours. Upon completing the reaction, 50 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. Column chromatography gave 2-isoamyl-2-isopropyl-1,3-propandiol dicinnamate as a yellow viacous liquid, and the yield was 51%. 1HNMR: δ (ppm) 0.88(d, 6H, CH3 of isoamyl), 0.99(d, 6H, CH3 of isopropyl), 1.21(m, 2H, CH2 of isoamy), 1.47(m, 2H, CH2 of isoamyl), 1.51(m, 1H, CH of isoamyl), 1.96(m, 1H, CH of isopropyl), 4.26(m, 4H, CH2O of 1,3-propandiol), 6.45(d, 2H, CH linked to carbonyl), 7.26-7.70(m, 12H, ArH and ═CH—)

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 4 hours
  4. additionwas added
  5. dissolutionto dissolve the resulting salt
  6. extractionThe mixture was extracted with ethyl acetate
  7. customThe organic phase was separated
  8. washwashed with saturated saline for two times
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed

Sources & evidence

ORD record
ord-26e817e428844f62875793870be909ba
Source dataset
uspto-grants-2008_06
Patent number
US07388061B2

Reaction notes

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