Pyridine → HCID 54355952, compound

HRID 971992Notes

Reaction equation

HRID 971992 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[C:2]#[CH:3].N1C=CC=CC=1.[CH:22]1([C:25](Cl)=[O:26])[CH2:24][CH2:23]1>CCOCC>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:25]([CH:22]1[CH2:24][CH2:23]1)=[O:26])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 21311698HCID 21311698, compound

Product 1

HCID 54355952HCID 54355952, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

91 g. of 10-(2-propynyloxy)-1-decanol are dissolved in 500 ml. of ether and treated with 37 g. of pyridine. While cooling with ice and stirring, there are added dropwise 49.5 g. of cyclopropane carboxylic acid chloride and 50 ml. of ether thereto. Subsequently, the mixture is stirred at room temperature for 3 hours. The mixture is poured onto ice-water, exhaustively extracted with ether and the extract is washed with 2 N hydrochloric acid, water, 10% potassium bicarbonate solution, semi-saturated and saturated sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/ethyl acetate (95:5 parts by volume) there is obtained pure cyclopropane carboxylic acid 10-(2-propynyloxy)decyl ester; nD25 =1.4616.

Workup

  1. temperatureWhile cooling with ice
  2. additionthere are added dropwise 49.5 g
  3. stirringSubsequently, the mixture is stirred at room temperature for 3 hours
  4. additionThe mixture is poured onto ice-water
  5. extractionexhaustively extracted with ether
  6. washthe extract is washed with 2 N hydrochloric acid, water, 10% potassium bicarbonate solution
  7. dry with materialsemi-saturated and saturated sodium chloride solution, dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-ece54bfbb5d143668c6f6b20a8b955cf
Source dataset
uspto-grants-1979_07
Patent number
US04162328

Reaction notes

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