N-Iodosuccinimide → Dibenzyl Methylthiomethyl Phosphate

HRID 264581Notes

Reaction equation

HRID 264581 reaction equation
[CH3:1][S:2][CH2:3][O:4]CSC.[P:8]([O-])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].IN1C(=O)CCC1=O>C1COCC1.C(OCC)(=O)C>[P:8]([O:4][CH2:3][S:2][CH3:1])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:9]

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 4193600DibenzylphosphateHCID 21902172(Methylsulfanyl)[(methylsulfanyl)methoxy]methane

Product 1

HCID 18423735Dibenzyl Methylthiomethyl PhosphateYield 75.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bis(methylthiomethyl)ether (30 mg, 2.34 mmol) and molecular sieves (300 mg) in THF (100 ml) at room temperature was added dibenzyl phosphate (2.74 g, 9.85 mmol) followed by N-iodosuccinimide (608 mg, 2.71 mmol) and the solution was stirred for 4 h. The reaction mixture was then diluted with ethyl acetate and filtered through a pad of celite. The filtrate was treated with a 1:1 (v:v) solution of saturated aqueous sodium bicarbonate and 5% aqueous sodium thiosulfate. The colorless organic extract was then washed with brine, dried over sodium sulfate and concentrated in vacuo to provide 600 mg (69%) of the title compound:

Workup

  1. filtrationfiltered through a pad of celite
  2. additionThe filtrate was treated with a 1:1 (v:v) solution of saturated aqueous sodium bicarbonate and 5% aqueous sodium thiosulfate
  3. extractionThe colorless organic extract
  4. washwas then washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24eeec41aee64ca0810a14ca9e3c6132
Source dataset
uspto-grants-1997_07
Patent number
US05646176

Reaction notes

Loading…