Sodium Bicarbonate → Di-tert-butyl (chloromethyl) phosphate
Reaction equation
[P:1]([O-:13])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[K+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.C([NH3+])CCC.C([NH3+])CCC.[Cl:35][CH2:36]OS(Cl)(=O)=O>C(Cl)Cl.O>[P:1]([O:13][CH2:36][Cl:35])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A 100 mL round bottomed flask was charged with potassium ditert-butyl phosphate (1.0 g, 4.03 mmol), sodium bicarbonate (677.4 mg, 8.06 mmol), n-butylammonium sulfate (68.2 mg, 0.403 mmol), water (10 ml) and methylene chloride (5 ml). To the mixture was added a solution of chloromethylchlorosulfonate (797.9 mg, 4.84 mmol) in methylene chloride (5 ml), and the mixture stirred at room temperature for 2 hours. To the reaction product was added water (30 ml), and the whole was extracted with methylene chloride (30 ml×3). The combined organic layers were washed with brine (30 ml), dried with Na2SO4, and solvent removed under reduced pressure. The residue was purified by column-chromatography (silica gel=80 g, hexane/ethyl acetate=1:1) to give di-t-butyl chloromethyl phosphate, as a colorless oil.
Workup
- extractionthe whole was extracted with methylene chloride (30 ml×3)
- washThe combined organic layers were washed with brine (30 ml)
- dry with materialdried with Na2SO4, and solvent
- customremoved under reduced pressure
- customThe residue was purified by column-chromatography (silica gel=80 g, hexane/ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-18fd615c8de6457a9c86ec76161b4d69
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158810B2
Reaction notes
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