Propargyl bromide → 1-(1-Propylcyclobutyl)but-3-yn-1-ol

HRID 2080903Notes

Reaction equation

HRID 2080903 reaction equation
[CH2:1](Br)[C:2]#[CH:3].[Mg].[CH2:6]([C:9]1([CH:13]=[O:14])[CH2:12][CH2:11][CH2:10]1)[CH2:7][CH3:8]>CCOCC>[CH2:6]([C:9]1([CH:13]([OH:14])[CH2:3][C:2]#[CH:1])[CH2:12][CH2:11][CH2:10]1)[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7842Propargyl bromide2×HCID 5462224MagnesiumHCID 143013561-Propylcyclobutane-1-carbaldehyde

Product 1

HCID 142547761-(1-Propylcyclobutyl)but-3-yn-1-olYield 250.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
40 °C

Procedure

Propargyl bromide (0.27 mL, 2.4 mmol) was added to a mixture of magnesium (1.1 g, 45 mmol) and mercuric chloride (30 mg, 0.117 mmol) in Et2O (60 mL). The mixture was warmed to 40° C. until bubbling commenced. The remainder of the propargyl bromide (2.1 mL, 19 mmol) was added in small portions. After ˜1.5 h the reaction became cloudy white. A solution of the aldehyde 3 (0.8 g, 7 mmol) in Et2O (4 mL) was added and the reaction was stirred for 16 h. The reaction was then quenched by cautiously adding saturated aqueous NH4Cl. The resultant mixture was extracted with Et2O. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 1:1 pentane/CH2Cl2) gave 1.0 g (94%) of the alcohol 4.

Workup

  1. customuntil bubbling
  2. customThe reaction was then quenched by cautiously adding saturated aqueous NH4Cl
  3. extractionThe resultant mixture was extracted with Et2O
  4. washThe organic portion was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d85a72e714084daf99dd02f202ed52ef
Source dataset
uspto-grants-2011_04
Patent number
US07932420B2

Reaction notes

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