Pyridine → HCID 54231568, compound

HRID 1658872Notes

Reaction equation

HRID 1658872 reaction equation
[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.N1C=C[CH:24]=[CH:23][CH:22]=1>C(OCC)C>[CH2:24]([O:5][C:4](=[O:6])[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:8][CH2:9][CH:10]([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:23]#[CH:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 53725805HCID 53725805, compound

Product 1

HCID 54231568HCID 54231568, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
22 °C

Procedure

1.6 g of 3,7-dimethyl-2,4-dodecadienoic acid is dissolved in 20 ml of absolute diethyl ether and 0.55 ml of pyridine. The resulting mixture is added dropwise over a period of about 10 minutes to 0.57 ml of thionyl chloride at a temperature between 0°C. and +10°C. Subsequently the mixture is stirred for 1 hour at room temperature (22°C.), then decanted off, and the residue is washed with absolute diethyl ether. The solution is evaporated to dryness under anhydrous conditions. The residue is dissolved in 10 ml of absolute diethyl ether. The ethereal solution is added dropwise at a temperature between 0°C. and +10°C., over a period of about 20 minutes, to a solution consisting of 0.56 ml of propargyl alcohol and 0.55 ml of pyridine in 10 ml of absolute ether. After stirring overnight (16 hours) at room temperature (22°C.) the mixture is diluted with diethyl ether, washed with 1-N hydrochloric acid, saturated aqueous sodium bicarbonate solution and finally with aqueous sodium chloride solution. After drying, the ethereal phase is evaporated. The crude product is chromatographed on a 30-fold amount of Kieselgel, using hexane/diethyl ether (19:1 parts by volume) as the eluant. There is obtained 3,7-dimethyl-2,4-dodecadienoic acid propargyl ester as a colorless oil; boiling point 105°C/0.05 mmHg (bulb tube); n25 25= 1.4951.

Workup

  1. customdecanted off
  2. washthe residue is washed with absolute diethyl ether
  3. customThe solution is evaporated to dryness under anhydrous conditions
  4. dissolutionThe residue is dissolved in 10 ml of absolute diethyl ether
  5. additionThe ethereal solution is added dropwise at a temperature between 0°C. and +10°C., over a period of about 20 minutes, to a solution
  6. stirringAfter stirring overnight (16 hours) at room temperature (22°C.) the mixture
  7. additionis diluted with diethyl ether
  8. washwashed with 1-N hydrochloric acid, saturated aqueous sodium bicarbonate solution and finally with aqueous sodium chloride solution
  9. customAfter drying
  10. customthe ethereal phase is evaporated
  11. customThe crude product is chromatographed on a 30-fold amount of Kieselgel

Sources & evidence

ORD record
ord-ef416f92070849aeb65b5edc6ff87b2f
Source dataset
uspto-grants-1976_06
Patent number
US03966780

Reaction notes

Loading…