Pyridine → 2-Decynyl cyclopropanecarboxylate

HRID 1731212Notes

Reaction equation

HRID 1731212 reaction equation
[CH2:1]([OH:11])[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1C=CC=CC=1.[CH:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1>CCOCC>[CH:18]1([C:21]([O:11][CH2:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[O:22])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 777632-Decyn-1-ol

Product 1

HCID 214954152-Decynyl cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.85 g. of 2-decyn-1-ol and 3.95 g. of pyridine in 100 ml. ether is added 3.0 g. of cyclopropanecarboxylic acid chloride. The mixture is stirred overnight under nitrogen. The reaction mixture is poured into distilled water, washed with dilute hydrochloric acid and then with sodium bicarbonate and solvent removed to yield 2-decynyl cyclopropanecarboxylate, b.p. 96°-97° (bath) at 0.1 mm.

Workup

  1. additionThe reaction mixture is poured
  2. distillationinto distilled water
  3. washwashed with dilute hydrochloric acid
  4. customwith sodium bicarbonate and solvent removed

Sources & evidence

ORD record
ord-e0af6a6589f043c7bce89d0001b10d60
Source dataset
uspto-grants-1976_11
Patent number
US03995054

Reaction notes

Loading…