Methanesulfonyl chloride → 3,4,5-Trimethoxybenzyl Mesylate

HRID 323258

Reaction equation

HRID 323258 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH2:6][OH:7].C(N(CC)C(C)C)(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(#N)C>[S:25]([O:7][CH2:6][C:5]1[CH:8]=[C:9]([O:13][CH3:14])[C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:27])(=[O:26])[CH3:24]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 774493,4,5-Trimethoxybenzyl alcoholHCID 81531Diisopropylethylamine

Product 1

HCID 184645913,4,5-Trimethoxybenzyl Mesylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 3,4,5-trimethoxybenzyl alcohol (9.0 g, 45.4 mmol), N,N-diisopropylethylamine (12.9 g, 100 mmol), and acetonitrile (60 mL). Cool in an ice bath. Add methanesulfonyl chloride (6.76 g, 49.0 mmol). After 2 hours, partition the reaction mixture between water and ethyl acetate. Separate the layers and extract the organic layer with 1 M hydrochloric acid solution and them a saturated solution of sodium bicarbonate. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureCool in an ice bath
  2. custompartition the reaction mixture between water and ethyl acetate
  3. customSeparate the layers
  4. extractionextract the organic layer with 1 M hydrochloric acid solution and them a saturated solution of sodium bicarbonate
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-fe813033fcf14a04924600f0eb5e1006
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Linked notes

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