1,4-Dichloro-2-butyne → HCID 54243264, compound

HRID 398773Notes

Reaction equation

HRID 398773 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][OH:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Cl:11][CH2:12][C:13]#[C:14][CH2:15]Cl.[H-].[Na+].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:15][C:14]#[C:13][CH2:12][Cl:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 131821,4-Dichloro-2-butyneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 76513Diethyl phosphonomethanol

Product 1

HCID 54243264HCID 54243264, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of hydroxymethylphosphonic acid diethylester (3.35 g, 20 mmol), 1,4-dichloro-2-butyne (3.8 g, 30 mmol) and tetra-n-butylammonium iodide,(0.75 g, 2 mmol) in anhydrous tetrahydrofuran (100 ml), sodium hydride (0.95 g, 24 mmol, 60% in oil) is added in portions at 0° C. The resulting mixture is stirred overnight at 0° C. Then the reaction mixture is stirred overnight at 20° C., hydrolyzed with a saturated solution of ammonium chloride and extracted with diethylether. The title product is obtained by flash chromatography on silica gel (2.3 g, 30%).

Workup

  1. additionis added in portions at 0° C
  2. extractionextracted with diethylether

Sources & evidence

ORD record
ord-ff822ecd195e400ea0895409b1883100
Source dataset
uspto-grants-1998_10
Patent number
US05817647

Reaction notes

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