Water → HCID 54060620, compound

HRID 1680854Notes

Reaction equation

HRID 1680854 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:14])[C:12]#[CH:13].N1C=CC=CC=1.[CH:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.O>C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([O:14][C:24]([CH:21]1[CH2:23][CH2:22]1)=[O:25])[C:12]#[CH:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 11423950HCID 11423950, compound

Product 1

HCID 54060620HCID 54060620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3.6 g of 1-(2-naphthyl)-2-propyn-1-ol and 1.6 g of pyridine are dissolved in 30 ml of methylene chloride, the solution is cooled to 0°-5° C. and a solution of 2.3 g of cyclopropane carboxylic acid chloride in 10 ml of methylene chloride is added with stirring. The mixture is left at room temperature for 2 hours, then poured into water and diluted with 50 ml of methylene chloride. The methylene chloride solution is separated and washed, in sequence, with 2 N hydrochloric acid solution, 10% potassium bicarbonate solution and a semi-saturated sodium chloride solution. The solution is then dried over sodium sulfate and evaporated. The crude product is purified by crystallization or by adsorption chromatography on silica gel to yield pure cyclopropane carboxylic acid 1-(2-naphthyl)-2-propynyl ester, m.p. 94°-96° C. (from cyclohexane).

Workup

  1. temperaturethe solution is cooled to 0°-5° C.
  2. customThe methylene chloride solution is separated
  3. washwashed, in sequence, with 2 N hydrochloric acid solution, 10% potassium bicarbonate solution
  4. dry with materialThe solution is then dried over sodium sulfate
  5. customevaporated
  6. customThe crude product is purified by crystallization or by adsorption chromatography on silica gel

Sources & evidence

ORD record
ord-947671d6fcc44f07961a58f971ded78c
Source dataset
uspto-grants-1981_06
Patent number
US04276305

Reaction notes

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