Water → 1-Benzylphosphorinane-1-oxide

HRID 2228188Notes

Reaction equation

HRID 2228188 reaction equation
[CH2:1]([P:8](=[O:15])(OCC)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCO[AlH2-]OCCOC.[Na+].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br.O>O1CCCC1>[CH2:1]([P:8]1(=[O:15])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 14122Diethyl benzylphosphonateHCID 16684438Red-Al

Product 1

HCID 184725391-Benzylphosphorinane-1-oxideYield 368.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl benzylphosphonate (2.5 g) in tetrahydrofuran (500 ml) was added Red-Al (70% toluene solution) (3.8 g) at room temperature, and the mixture was stirred until gas production stopped. To the reaction mixture was added 1,5-dibromopentane (25.18 g), and the mixture was stirred at 50-60° C. for 16 hours. To the reaction mixture was added water (20 ml), and precipitate was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was separated and purified with column chromatography (ethyl acetate ethanolethyl acetate=1:2) to give 1-benzylphosphorinane-1-oxide (8.41 g) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at 50-60° C. for 16 hours
  2. customwas removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was separated
  5. custompurified with column chromatography (ethyl acetate ethanolethyl acetate=1:2)

Sources & evidence

ORD record
ord-6b302083ccd0451797d41206ba8a0d59
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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