Hydrochloric Acid → HCID 13387950, compound

HRID 580662Notes

Reaction equation

HRID 580662 reaction equation
[Mg].[CH2:2](Br)[C:3]#[CH:4].[CH:6]1([CH2:9][CH2:10][C:11](=[O:13])[CH3:12])[CH2:8][CH2:7]1.Cl>CCOCC.O1CCCC1>[CH3:12][C:11]([OH:13])([CH2:10][CH2:9][CH:6]1[CH2:8][CH2:7]1)[CH2:4][C:3]#[CH:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7842Propargyl bromide2×HCID 5462224MagnesiumHCID 133879494-CYCLOPROPYL 2-BUTANONE

Product 1

HCID 13387950HCID 13387950, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 1 part by volume of magnesium in 25 parts by volume of tetrahydrofuran under argon is added a small amount of propargyl bromide and mercuric chloride to initiate reaction. Once the reaction is started 6.3 parts of propargyl bromide and 36 parts of 4-cyclopropyl-2-butanone in 50 parts by volume of tetrahydrofuran is added dropwise so as to maintain reflux. Upon completion of the reaction, the reaction mixture is cooled to room temperature and poured into a mixture of ether and 1N HCl. The aqueous layer is extracted twice with ether. The ether extracts are combined and washed 3 times with water and one time with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and evaporated to provide a residual oil. The residual oil is distilled under high vacuum to provide 4-methyl-4-hydroxy-6-cyclopropyl-hex-1-yne.

Workup

  1. customreaction
  2. additionis added dropwise so as
  3. temperatureto maintain
  4. temperaturereflux
  5. customUpon completion of the reaction
  6. extractionThe aqueous layer is extracted twice with ether
  7. washwashed 3 times with water and one time with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customto provide a residual oil
  12. distillationThe residual oil is distilled under high vacuum

Sources & evidence

ORD record
ord-e46e62890de949afbc4e6bdc1c85dada
Source dataset
uspto-grants-1988_06
Patent number
US04754059

Reaction notes

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