Methanesulfonyl chloride → 3,4,5-Trimethoxybenzyl Mesylate

HRID 637042

Reaktionsgleichung

Reaktionsgleichung von HRID 637042
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 184645913,4,5-Trimethoxybenzyl Mesylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-29826fabea994dc48c092b20a9be0cd1
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194406B1

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