Propargyl bromide → HCID 131719442, compound

HRID 1733825Notes

Reaction equation

HRID 1733825 reaction equation
[CH3:1][C:2]([CH:4]=[P:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:24]([Li])[CH2:25][CH2:26]C.C(Br)C#C>O1CCCC1>[CH2:1]([C:2]([CH:4]=[P:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:3])[CH2:26][C:25]#[CH:24]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 178418339Butyllithium

Product 1

HCID 131719442HCID 131719442, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.0 g of methylcarbonylmethylenetriphenyl phosphorane is dissolved in 628 ml of tetrahydrofuran and mixed by instillation at -78° C. with 41.3 ml of butyllithium (1.6 molar solution in hexane). Then,5.0 ml of propargyl bromide is instilled. The reaction mixture is added to an ice/common salt solution after heating to room temperature, and the mixture is extracted with ethyl acetate. After drying the organic phase with sodium sulfate,23.4 g of solid is obtained. Column chromatographic purification (silica gel/ethyl acetate) yields 15.4 g of the title compound with a melting point of 135°-136° C.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialAfter drying the organic phase with sodium sulfate

Sources & evidence

ORD record
ord-1dd9ab5f52634be89f51795ca8d7feb3
Source dataset
uspto-grants-1996_07
Patent number
US05532228

Reaction notes

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