Propargyl bromide → HCID 18412031, compound

HRID 992450Notes

Reaction equation

HRID 992450 reaction equation
C([Li])CCC.C(N[CH:10]([CH3:12])[CH3:11])(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[O:24][C:23]([CH3:26])([CH3:25])[O:22][C:21]2=[O:27])=[CH:16][CH:15]=1.C(Br)C#C>O1CCCC1>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2([CH2:12][C:10]#[CH:11])[O:24][C:23]([CH3:25])([CH3:26])[O:22][C:21]2=[O:27])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 7842Propargyl bromideHCID 7912DiisopropylamineHCID 10775653HCID 10775653, compoundHCID 178418339Butyllithium

Product 1

HCID 18412031HCID 18412031, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3.3 ml of butyl lithium (1.6 molar in hexane) are added under stirring to a solution of 0.8 ml diisopropylamine in 20 ml tetrahydrofurane at −78° C. under nitrogen. After stirring for 30 minutes at the same temperature, 1.13 g of 5-(4-chloro-phenyl )-2,2-dimethyl-(1,3)-dioxolan-4-one in 5 ml tetrahydrofurane are added and stirring is continued for 1.5 hours. Then the reaction mixture is treated with a solution of 0.57 ml propargyl bromide in 3 ml tetrahydrofurane. Stirring is continued at about 60° C. over the night. Then the reaction is quenched with HCl 1N (pH 6) and ice and water and extracted with diethyl ether. The extracts are dried over sodium sulfate and evaporated. The 5-(4-chloro-phenyl)-2,2-dimethyl-5-prop-2-ynyl-(1,3)dioxolan-4-one remains as a oil which is used directly for the next step.

Workup

  1. additionare added
  2. stirringStirring
  3. customis continued at about 60° C. over the night
  4. customThen the reaction is quenched with HCl 1N (pH 6) and ice and water
  5. extractionextracted with diethyl ether
  6. dry with materialThe extracts are dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-3b0a3608dc1748cf8df2beba08d96d1d
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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