Hydrochloric Acid → HCID 4651150, compound

HRID 1065143Notes

Reaction equation

HRID 1065143 reaction equation
[CH2:1]([Li])[CH2:2]CC.C([Si](C#C)(CC)CC)C.[CH2:15]([CH2:22][C:23](=[O:25])[CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CCOCC>[CH3:24][C:23]([OH:25])([CH2:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:1]#[CH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 17355Benzyl acetoneHCID 637947(Triethylsilyl)acetyleneHCID 178418339Butyllithium

Product 1

HCID 4651150HCID 4651150, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

8 Parts by volume of 2.5 molar n-butyl lithium is added to a solution of 3.1 parts of triethylsilyl acetylene in 20 parts by volume of ethyl ether at -30° C. The resulting solution is allowed to warm to room temperature, then it is cooled again to -30° C. and 3 parts of benzyl acetone is added. The reaction mixture is allowed to warm to room temperature and is then stirred for 1 hour. The reaction mixture is poured into ether and dilute hydrochloric acid. The ethereal layer is washed with water and dried over anhydrous sodium sulfate. The ether is removed under reduced pressure and the residual oil is dissolved in 15 parts by volume of dimethylformamide containing 2 parts of powdered potassium fluoride. This reaction mixture is stirred and heated at 70°-80° C. for 1 hour, after which time it is diluted with water and extracted with ether. The ether layer is separated and washed with water and dried over anhydrous sodium sulfate. The ether is removed under reduced pressure and the residue is chromatographed on silica gel using 30% ethyl acetate/hexane as eluent to provide 3-methyl-3-hydroxy-5-phenyl-1-pentyne.

Workup

  1. temperatureit is cooled again to -30° C.
  2. temperatureto warm to room temperature
  3. washThe ethereal layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe ether is removed under reduced pressure
  6. dissolutionthe residual oil is dissolved in 15 parts by volume of dimethylformamide containing 2 parts of powdered potassium fluoride
  7. stirringThis reaction mixture is stirred
  8. temperatureheated at 70°-80° C. for 1 hour
  9. additionafter which time it is diluted with water
  10. extractionextracted with ether
  11. customThe ether layer is separated
  12. washwashed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe ether is removed under reduced pressure
  15. customthe residue is chromatographed on silica gel using 30% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-3eb3aea2c7ea4cc790b0593aaa222ffa
Source dataset
uspto-grants-1982_05
Patent number
US04328355

Reaction notes

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