Propargyl bromide → HCID 12138950, compound

HRID 2287611Notes

Reaction equation

HRID 2287611 reaction equation
[CH:1]([N-]C(C)C)(C)[CH3:2].[Li+].C[C:10]1([CH3:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:17].C(Br)C#C.[Cl-].[NH4+]>C1COCC1>[CH2:18]([CH:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[O:17])[C:1]#[CH:2]

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 12648913HCID 12648913, compound

Product 1

HCID 12138950HCID 12138950, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium diisopropylamide (LDA) in THF (50 ml) was added to a solution of 2,2-dimethylcycloheptanone (13) (10.55 g, 75.37 mmol) in THF (30 ml) at a temperature of 0° C. The mixture was stirred at room temperature for one hour. To this was added dropwise propargylbromide (6.85 ml, 90.44 mmol) at 0° C. The mixture was stirred at room temperature for one hour, and then heated at 50° C. for 3 hours. The mixture was treated with an aqueous ammonium chloride solution, and then purified by distillation (100° C., 2 mmHg) to obtain propargyl-cycloheptanone (14) (7.34 g, 55%).

Workup

  1. stirringThe mixture was stirred at room temperature for one hour
  2. temperatureheated at 50° C. for 3 hours
  3. distillationpurified by distillation (100° C., 2 mmHg)

Sources & evidence

ORD record
ord-ad1043f39ef84609b78ae043f9edf453
Source dataset
uspto-grants-2000_07
Patent number
US06084043

Reaction notes

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