2,4,6-Trimethylpyridine → Methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl ester

HRID 2707

Reaktionsgleichung

Reaktionsgleichung von HRID 2707
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][OH:11].N1C(C)=CC(C)=CC=1C.[Cl-:21].[Li+].[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>CN(C)C=O>[Cl:21][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][O:11][S:23]([CH3:26])(=[O:25])=[O:24]

Komponenten

6

Edukt 4

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 2390242-[2-(Hydroxymethyl)phenyl]ethanolHCID 433294Lithium Chloride

Produkt 1

HCID 54328826Methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl esterAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Mix 2-(2-hydroxymethyl-phenyl)-ethanol (12.0 g, 78.8 mmol) and collidine (23 mL, 0.17 mol) and treat with lithium chloride (7.35 g, 0.173 mmol) in dimethylformamide (125 mL). Cool in an ice bath and treat, by dropwise addition, with mesyl chloride (13.4 mL). Stir at 0° C. for 4 hours, partition between ice water (300 mL) and a 1:1 mixture of ether:pentane (2×400 mL). Wash the organic layer with a saturated solution of CuSO4 (2×200 mL), dry (MgSO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate) to give the title compound as a pale yellow oil (8.8 g, 45%).

Aufarbeitung

  1. temperatureCool in an ice bath
  2. custompartition between ice water (300 mL)
  3. additiona 1:1 mixture of ether
  4. washWash the organic layer with a saturated solution of CuSO4 (2×200 mL)
  5. dry with materialdry (MgSO4)
  6. custompurify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d530a516b02640fda96b3ced16ffaeab
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731306

Verknüpfte Notizen

Wird geladen…