Methanesulfonyl chloride → HCID 86697129, compound

HRID 237466Notes

Reaction equation

HRID 237466 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][CH2:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11].C(N(CC)C(C)C)(C)C>ClCCl>[CH3:1][S:2]([O:11][CH2:10][C:9]([CH3:13])([CH3:12])[CH2:8][O:7][CH3:6])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 1434401-Propanol, 3-methoxy-2,2-dimethyl-

Product 1

HCID 86697129HCID 86697129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (330 mL) is added dropwise to a solution of 3-methoxy-2,2-dimethylpropan-1-ol (250 mg) and N,N-diisopropylethylamine (1.1 mL) in dichloromethane (3 mL) chilled in an ice bath. The mixture is stirred at room temperature for 12 hours and partitioned between saturated aqueous NaHCO3 solution and dichloromethane. The organic phase is washed with twice with 1 N hydrochloric acid, saturated aqueous NaHCO3 solution and brine. Then the organic phase is dried (MgSO4) and concentrated to give the title compound. Yield: 407 mg; TLC: rf=0.75 (silicagel, cyclohexane/ethyl acetate 3:1).

Workup

  1. temperaturechilled in an ice bath
  2. custompartitioned between saturated aqueous NaHCO3 solution and dichloromethane
  3. washThe organic phase is washed with twice with 1 N hydrochloric acid, saturated aqueous NaHCO3 solution and brine
  4. dry with materialThen the organic phase is dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b931a610c0b144d28b45017ec1fc3e87
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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