Water → HCID 23415569, compound

HRID 1737284Notes

Reaction equation

HRID 1737284 reaction equation
[H-].[Na+].[CH2:3]([P:14](=[O:23])([O:19][CH:20]([CH3:22])[CH3:21])[O:15][CH:16]([CH3:18])[CH3:17])[P:4](=[O:13])([O:9][CH:10]([CH3:12])[CH3:11])[O:5][CH:6]([CH3:8])[CH3:7].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].O>O1CCCC1>[CH:20]([O:19][P:14]([O:15][CH:16]([CH3:18])[CH3:17])([CH:3]([P:4]([O:9][CH:10]([CH3:11])[CH3:12])([O:5][CH:6]([CH3:8])[CH3:7])=[O:13])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 74266Tetraisopropyl methylenediphosphonate

Product 1

HCID 23415569HCID 23415569, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 60% sodium hydride (0.132 g) was suspended in dry tetrahydrofuran (4 ml), and tetraisopropyl methylenebisphosphonate (1.1 g) was added dropwise thereto at room temperature. After stirring for 10 minutes, ethyl bromoacetate (0.354 ml) was added dropwise thereto and the resulting mixture was stirred at the same temperature for 1 hour. Water was added thereto, followed by extraction (twice) with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (methanol:methylene chloride=2:98) to obtain ethyl 3,3-bis(diisopropoxyphosphinoyl)propionate (0.37 g, yield 27%).

Workup

  1. customat room temperature
  2. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  3. extractionfollowed by extraction (twice) with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (methanol:methylene chloride=2:98)

Sources & evidence

ORD record
ord-641994387a194ebc8981e772e721e56e
Source dataset
uspto-grants-1999_10
Patent number
US05962438

Reaction notes

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