Methyl Methanesulfonate → HCID 59497603, compound

HRID 1747422Notes

Reaction equation

HRID 1747422 reaction equation
[CH3:1][O:2][S:3]([CH3:6])(=[O:5])=[O:4].[Li]CCCC.[CH2:12]([O:14][P:15](Cl)(=[O:19])[O:16][CH2:17][CH3:18])[CH3:13].[NH4+].[Cl-]>C1COCC1.CCCCCC.O>[CH3:1][O:2][S:3]([CH2:6][P:15]([O:16][CH2:17][CH3:18])([O:14][CH2:12][CH3:13])=[O:19])(=[O:5])=[O:4]

Participants

8

Reactant 4

HCID 4156Methyl MethanesulfonateHCID 13139Diethyl chlorophosphateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 59497603HCID 59497603, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methanesulfonic acid methyl ester (0.43 mL, 5.0 mmol) is dissolved in THF (10 mL) and it is cooled down to −78° C. 1.6 M n-BuLi (3.4 mL, 5.5 mmol) in hexane is added into it dropwise and the mixture is stirred for 30 min at −78° C. Then Phosphorochloridic acid diethyl ester (0.41 mL, 2.8 mmol) is added dropwise into the mixture and it is then gradually warmed up to −50° C. in 2 hrs. 5 mL of sat. NH4Cl and 20 mL of water are added and it is further warmed up to room temperature. The mixture is extracted with EtOAc (3×40 mL) and the organic layers are combined, dried (Na2SO4) and concentrated to give crude product. Purification by flash column chromatography affords 350 mg (53%) of (Diethoxy-phosphoryl)-methanesulfonic acid methyl ester.

Workup

  1. temperatureis then gradually warmed up to −50° C. in 2 hrs
  2. temperatureit is further warmed up to room temperature
  3. extractionThe mixture is extracted with EtOAc (3×40 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give crude product
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-7acb264e37ba41c190992246ce869862
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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