N,N,N',N'-Tetramethylethylenediamine → HCID 11096651, compound

HRID 896005Notes

Reaction equation

HRID 896005 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(CCN(C)C)C.[Li]CCCC.[P:22](Cl)([O:27][CH2:28][CH3:29])([O:24][CH2:25][CH3:26])=[O:23]>C1COCC1>[CH2:25]([O:24][P:22]([C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O:27][CH2:28][CH3:29])=[O:23])[CH3:26]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10821PhenylacetyleneHCID 13139Diethyl chlorophosphateHCID 178418339Butyllithium

Product 1

HCID 11096651HCID 11096651, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of phenylacetylene (1 mmole) in anhydrous THF (5 mL) was treated with TMEDA (1.2 mmole) followed by n-BuLi (1.2 mmole) at −78° C. After 30 min the reaction was treated with diethyl chlorophosphate, and the resulting solution was stirred at −78° C. for 1 h. The reaction was quenched with saturated ammonium chloride. Extraction and chromatography gave 1-diethylphosphono-2-phenylacetylene as an oil.

Workup

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionExtraction and chromatography

Sources & evidence

ORD record
ord-47f7c63c462d45aca1dae9a67c01d148
Source dataset
uspto-grants-2005_07
Patent number
US06919322B2

Reaction notes

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