1-Bromo-2-methylpropane → Tertiary-butyl(iso-butyl)(diethoxymethyl)phosphine oxide

HRID 36455Notes

Reaction equation

HRID 36455 reaction equation
[H-].[Na+].[C:3]([PH:7](=[O:15])[CH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([CH3:6])([CH3:5])[CH3:4].[CH2:16](Br)[CH:17]([CH3:19])[CH3:18]>O1CCCC1>[C:3]([P:7](=[O:15])([CH2:16][CH:17]([CH3:19])[CH3:18])[CH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([CH3:5])([CH3:4])[CH3:6]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 178472281HCID 178472281, compound

Product 1

HCID 19938716Tertiary-butyl(iso-butyl)(diethoxymethyl)phosphine oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Dry sodium hydride (0.42 g) is suspended in 50 ml of dry tetrahydrofuran under an argon atmosphere. To this stirred suspension is added 3.6 g (0.017 mol) of tertiary-butyl(diethoxymethyl)-phosphine oxide dissolved in 25 ml of dry tetrahydrofuran, at room temperature. Stirring is continued for 10 minutes at room temperature, during which time the solid dissolves and a gas is evolved. To the clear solution obtained is added a solution of 2.4 g (0.017 mol) of iso-butyl bromide in 25 ml of dry tetrahydrofuran. After the addition is complete, the reaction mixture is heated under reflux for 15 hours, then allowed to cool at room temperature and washed with 20 ml of water. The organic extracts are dried and evaporated under reduced pressure. The crude product is purified by chromatography on silica using ethyl acetate as eluent to give tertiary-butyl-(iso-butyl)(diethoxymethyl)phosphine oxide as a colourless oil.

Workup

  1. dissolutionthe solid dissolves
  2. customTo the clear solution obtained
  3. additionAfter the addition
  4. temperaturethe reaction mixture is heated
  5. temperatureunder reflux for 15 hours
  6. washwashed with 20 ml of water
  7. customThe organic extracts are dried
  8. customevaporated under reduced pressure
  9. customThe crude product is purified by chromatography on silica

Sources & evidence

ORD record
ord-19eaa368821f44b99ed7b53b2481f733
Source dataset
uspto-grants-1995_05
Patent number
US05414133

Reaction notes

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