Water → HCID 23454865, compound

HRID 1680859Notes

Reaction equation

HRID 1680859 reaction equation
C(OC([C:7]1([O:17][CH2:18][C:19]#[CH:20])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH2:8]1)=O)C#C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[O:28]1CCC[CH2:29]1>>[CH2:18]([O:17][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:29][OH:28])[C:19]#[CH:20]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 86737824HCID 86737824, compound

Product 1

HCID 23454865HCID 23454865, compound

Procedure

14.55 g of 1-(2-propynyloxy)-naphthoic acid 2-propynyl ester dissolved in 50 ml of absolute tetrahydrofuran are cautiously added at -10° C. under a nitrogen atmosphere to a suspension of 2.09 g of lithium aluminum hydride in 200 ml of absolute tetrahydrofuran. After completion of the addition is complete, the mixture is left to react at about 0° C. for a further 1 hour. To hydrolyze, water is cautiously added dropwise at -10° C. with stirring while the temperature is maintained at 0° C. or below. The mixture is filtered using a filter aid (Celite) and the filtrate is concentrated. The residue is dissolved in ethyl acetate and washed, in sequence, with 2 N hydrochloric acid solution, 10% potassium bicarbonate solution, semi-saturated and saturated sodium chloride solution. The residue is dried over sodium sulfate and evaporated. Pure [1-(2-propynyloxy)-2-naphthyl]methanol, m.p. 65°-68° C. (from hexane/ethyl acetate), is obtained by recrystallization. This material is reacted with cyclopropane carboxylic acid chloride in the procedure described in Example 2 to yield cyclopropane carboxylic acid [1-(2-propynyloxy)-2-naphthyl]methyl ester; nD20 =1.5902.

Workup

  1. additionAfter completion of the addition
  2. waitthe mixture is left
  3. customto react at about 0° C. for a further 1 hour
  4. temperatureis maintained at 0° C. or below
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated
  7. dissolutionThe residue is dissolved in ethyl acetate
  8. washwashed, in sequence, with 2 N hydrochloric acid solution, 10% potassium bicarbonate solution
  9. dry with materialThe residue is dried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-a4af880cec8c41a79191f95761356a56
Source dataset
uspto-grants-1981_06
Patent number
US04276305

Reaction notes

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