Sodium hydride → HCID 86587036, compound

HRID 398771Notes

Reaction equation

HRID 398771 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]/[CH:13]=[CH:14]\[CH2:15]Cl.[H-].[Na+].[Cl-].[NH4+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:15]/[CH:14]=[CH:13]\[CH2:12][Cl:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 76513Diethyl phosphonomethanolHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 86587036HCID 86587036, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of hydroxymethyl phosphonic acid diethylester (1.68 g, 10 mmol), Z-1,4-dichloro-2-butene (1.9 g, 15 mmol) and tetra-n-butylammonium iodide (0.36 g, 1 mmol) in anhydrous tetrahydrofuran (15 ml), sodium hydride (0.48 g, 12 mmol, 60% in oil) is added at 0° C. The resulting 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 (1.2 g, 45%).

Workup

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

Sources & evidence

ORD record
ord-f3a35720baf943ee80a3392cf1ad26e8
Source dataset
uspto-grants-1998_10
Patent number
US05817647

Reaction notes

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