Water → 1-Methanesulfonyloxy-2-(diethylphosphonomethoxy)ethane

HRID 1459167Notes

Reaction equation

HRID 1459167 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:11][CH2:12][OH:13])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>C(Cl)Cl>[CH3:21][S:22]([O:13][CH2:12][CH2:11][O:10][CH2:9][P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10262588Diethyl 2-hydroxyethoxymethanephosphonate

Product 1

HCID 145409811-Methanesulfonyloxy-2-(diethylphosphonomethoxy)ethaneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-diethylphosphonomethoxy-1-ethanol (40.7 g, 192 mmol) in 500 mL of CH2Cl2 was cooled to 0° C. and then triethylamine (29.1 g, 288 mmol) was added in one portion, followed by addition of methanesulfonyl chloride (26.4 g, 230 mmol) dropwise over 20 min. The reaction mixture was kept at 0° C. for 0.5 hours and then poured into water. The aqueous phase was extracted with two portions of CH2 Cl2 and the combined organic phases dried over MgSO4, filtered and concentrated to afford 54.4 g (98%) of 1-methanesulfonyloxy-2-(diethylphosphonomethoxy)ethane as a clear, pale orange oil. The mesylate could be employed without purification or purified by column chromatography on silica gel (5% methanol in CH2 Cl2).

Workup

  1. extractionThe aqueous phase was extracted with two portions of CH2 Cl2
  2. dry with materialthe combined organic phases dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b598f0f43e38460d8a645462f9c6c6ae
Source dataset
uspto-grants-1998_12
Patent number
US05854228

Reaction notes

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