Methyl Ethyl Ketone → HCID 53883385, compound

HRID 1680860Notes

Reaction equation

HRID 1680860 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=O.C(=O)([O-])[O-:17].[K+].[K+].[CH2:22](Br)[C:23]#[CH:24].[CH2:26]([C:28]([CH3:30])=O)C>>[CH2:22]([O:15][C:14]1[C:5]([CH2:3][O:2][C:1]([CH:26]2[CH2:28][CH2:30]2)=[O:17])=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:23]#[CH:24]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 70163Methyl 3-hydroxy-2-naphthoate

Product 1

HCID 53883385HCID 53883385, compound

Procedure

20.2 g of 3-hydroxy-2-naphthoic acid methyl ester are dissolved in 200 ml of methyl ethyl ketone and 27.6 g of potassium carbonate and 23.6 g of propargyl bromide are added thereto with stirring and under a nitrogen atmosphere. The heterogeneous mixture is refluxed overnight and then filtered. The filtrate is concentrate in vacuo and the residue is poured into 250 ml of ice-water and extracted three times with hexane/ethyl acetate (1:1). The extracts are washed with 2 N hydrochloric acid solution, 10% potassium bicarbonate solution, semi-saturated and saturated sodium chloride solution, dried and evaporated on a rotary evaporator. The product 3-(2-propynyloxy)-2-naphthoic acid methyl ester is reduced, without further purification, with lithium aluminum hydride by the process described in Example 7. The resulting [3-(2-propynyloxy)-2-naphthyl]methanol is reacted directly with cyclopropane carboxylic acid chloride by the process described in Example 2 to yield cyclopropane carboxylic acid [3-(2-propynyloxy)-2-naphthyl]methyl ester of melting point 58°-60° C.

Workup

  1. temperatureThe heterogeneous mixture is refluxed overnight
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrate in vacuo
  4. additionthe residue is poured into 250 ml of ice-water
  5. extractionextracted three times with hexane/ethyl acetate (1:1)
  6. washThe extracts are washed with 2 N hydrochloric acid solution, 10% potassium bicarbonate solution
  7. dry with materialsemi-saturated and saturated sodium chloride solution, dried
  8. customevaporated on a rotary evaporator
  9. customThe product 3-(2-propynyloxy)-2-naphthoic acid methyl ester is reduced, without further purification, with lithium aluminum hydride by the process
  10. customThe resulting [3-(2-propynyloxy)-2-naphthyl]methanol is reacted directly with cyclopropane carboxylic acid chloride by the process

Sources & evidence

ORD record
ord-3d36088675c54fb5981c8bb6b7c466b9
Source dataset
uspto-grants-1981_06
Patent number
US04276305

Reaction notes

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