Pyridine → Prop-2-yn-1-yl tetradecanoate

HRID 1973262Notes

Reaction equation

HRID 1973262 reaction equation
[C:1]([OH:16])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].S(Cl)(Cl)=O.CN(C)C=O.[CH2:26](O)[C:27]#[CH:28].N1C=CC=CC=1>O.CCOCC>[C:1]([O:16][CH2:28][C:27]#[CH:26])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 7859Propargyl alcoholHCID 11005Myristic AcidHCID 24386Thionyl Chloride

Product 1

HCID 13216323Prop-2-yn-1-yl tetradecanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3.00 g. (13.5 mmoles) of tetradecanoic acid in 40 ml. of dry ether at 0° is added 1.42 ml. (19.74 mmoles) of thionyl chloride and 0.2 ml (2.63 mmoles) of dimethylformamide. The solution is allowed to warm to room temperature and then is stirred for 21/2 hours. The solvent is removed from the top layer of the now biphasic mixture by evaporation and the residue is taken up in 30 ml. of ether. To this solution at 0° under nitrogen is added 1.15 ml. (19.75 mmoles) of propargyl alcohol and 2.1 ml. (2.0 mmoles) of pyridine. The reaction mixture is allowed to warm to room temperature and stirred for one day, ether and water are then added, the organic phase separated, the aqueous phase extracted with ether, and the combined organic phases washed with 3N sulfuric acid, 10% aqueous sodium carbonate, water, saturated aqueous copper sulfate, water and brine. The reaction mixture is dried over calcium sulfate and concentrated to yield propargyl tetradecanoate, boiling at 125° at 0.25 mm.

Workup

  1. customThe solvent is removed from the top layer of the now biphasic mixture by evaporation
  2. additionTo this solution at 0° under nitrogen is added 1.15 ml
  3. temperatureto warm to room temperature
  4. stirringstirred for one day
  5. customthe organic phase separated
  6. extractionthe aqueous phase extracted with ether
  7. washthe combined organic phases washed with 3N sulfuric acid, 10% aqueous sodium carbonate, water, saturated aqueous copper sulfate, water and brine
  8. dry with materialThe reaction mixture is dried over calcium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-268a32de9f424a2e8bb5da4c4a09e40f
Source dataset
uspto-grants-1976_12
Patent number
US03996380

Reaction notes

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