Lithium borohydride → (5-Chloro-2-(methylsulfonyl)phenyl)methanol

HRID 1013950Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013950
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[BH4-].[Li+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([CH2:7][OH:8])[CH:11]=1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 66877882Methyl 5-chloro-2-(methylsulfonyl)benzoate

Produkt 1

HCID 66885987(5-Chloro-2-(methylsulfonyl)phenyl)methanolAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(Step 2) To a solution of methyl 5-chloro-2-(methylsulfonyl)benzoate obtained in Step 1 (2.65 g) in tetrahydrofuran-ethanol (50 ml+5 ml) was added lithium borohydride (348 mg) at 0° C. The mixture was stirred at 60° C. for 2 hr, treated with ice, and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to give [5-chloro-2-(methylsulfonyl)phenyl]methanol (2.1 g).

Aufarbeitung

  1. additiontreated with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed successively with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-25b325d19ca849cca994a74d7d315fb4
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07982044B2

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