Methanesulfonyl chloride → 2-[(3-Cyanobenzyl)oxy]ethyl methanesulfonate

HRID 916849Notes

Reaction equation

HRID 916849 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].C(N(C(C)C)CC)(C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:8]([C:9]#[N:10])[CH:7]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 284140323-[(2-Hydroxyethoxy)methyl]benzonitrile

Product 1

HCID 858813992-[(3-Cyanobenzyl)oxy]ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(2-hydroxyethoxy)methyl]benzonitrile (example 28vi) (6.00 g) and diisopropylethylamine (11.8 ml) in dichloromethane (100 ml) at 0° C. was added methanesulphonyl chloride (3.14 ml) dropwise and the mixture allowed to stir for 2 h. The resultant mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate. The organic phase was dried (MgSO4) and concentrated in vacuo to give the title compound (8.5 g). LCMS RT=2.58 min.

Workup

  1. customat 0° C.
  2. customThe resultant mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3eea76d6a04b421aa5dbf77cba9a1981
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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