Propargyl bromide → 4-Cyclopropyl-4-hydroxy-1-octyne

HRID 66408Notes

Reaction equation

HRID 66408 reaction equation
[Mg].[CH:2]1([C:5]([CH2:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH2:4][CH2:3]1.[CH2:11](Br)[C:12]#[CH:13].[Cl-].[NH4+]>CCOCC>[CH:2]1([C:5]([OH:6])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:13][C:12]#[CH:11])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11029852n-Butyl cyclopropyl ketone

Product 1

HCID 130787514-Cyclopropyl-4-hydroxy-1-octyne

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a stirred, refluxing suspension of amalgam prepared from 6.2 g of magnesium and 50 mg of mercuric chloride suspended in 60 ml of ether is added a solution of a mixture of 30.4 g of n-butyl cyclopropyl ketone (Example 8) and 29.8 g of propargyl bromide in 65 ml of ether during 60 minutes. After reaction at reflux temperature for an additional 30 minutes, the mixture is cooled to 0° and treated with 35 ml of saturated ammonium chloride. The mixture is diluted with ether and filtered through Celite. The filtrate is washed with brine, dried over potassium carbonate, and concentrated. The residue is distilled to provide a liquid, b.p. 93°-94° C (12 mm), pmr spectrums (C D Cl3):δ0.43 (cyclopropyl hydrogens), 2.07 (triplet, HC≡C), and 2.44 (doublet, C≡CCH2).

Workup

  1. temperatureTo a stirred, refluxing
  2. additionis added
  3. customAfter reaction
  4. temperatureat reflux temperature for an additional 30 minutes
  5. temperaturethe mixture is cooled to 0°
  6. filtrationfiltered through Celite
  7. washThe filtrate is washed with brine
  8. dry with materialdried over potassium carbonate
  9. concentrationconcentrated
  10. distillationThe residue is distilled
  11. customto provide a liquid, b.p. 93°-94° C (12 mm), pmr spectrums (C D Cl3)

Sources & evidence

ORD record
ord-dfdcf5bec9e449c19bf14fc6d875b882
Source dataset
uspto-grants-1978_12
Patent number
US04131737

Reaction notes

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