Sodium hydride → HCID 54403749, compound

HRID 266236Notes

Reaction equation

HRID 266236 reaction equation
[H-].[Na+].[CH2:3]([O:5][P:6]([O-:10])[O:7][CH2:8][CH3:9])[CH3:4].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17]Cl>CCCCC>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][P:6]([O:7][CH2:8][CH3:9])([O:5][CH2:3][CH3:4])=[O:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3780918DiethylphosphiteHCID 53879945HCID 53879945, compound

Product 1

HCID 54403749HCID 54403749, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a slurry of 6.26 g (149 mmol) of 57% NaH and 300 mL of n-pentane at 0° C. was added 17.14 g (124 mmol) of diethylphosphite and the mixture was stirred for 1 hour at 0°. The mixture was then cooled to -70° and 25 g (124 mmol) of 1-bromo-4-(chloromethoxy)butane was added and the reaction mixture warmed to 0° and stirred for 1 hour. The mixture was then filtered and evaporated. The residue was purified by SiO2 chromatography to give 26 g (70%) of 1-bromo-4-(diethylphosphonomethoxy)butane as a colorless oil.

Workup

  1. temperatureThe mixture was then cooled to -70°
  2. temperaturethe reaction mixture warmed to 0°
  3. stirringstirred for 1 hour
  4. filtrationThe mixture was then filtered
  5. customevaporated
  6. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-87ec84fbb765463f831f7d5104152bce
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Reaction notes

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