Lithium borohydride → [2-(Cyclopentylsulfonyl)phenyl]methanol

HRID 447848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 447848
[CH:1]1([S:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11](OC)=[O:12])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Li+]>O1CCCC1CCO>[CH:1]1([S:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[CH2:11][OH:12])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 66877458Methyl 2-(cyclopentylsulfonyl)benzoate

Produkt 1

HCID 66877106[2-(Cyclopentylsulfonyl)phenyl]methanolAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(Step 2) To a solution of methyl 2-(cyclopentylsulfonyl)benzoate obtained in Step 1 (4.1 g) in tetrahydrofuran-ethanol (100 ml+10 ml) was added lithium borohydride (500 mg) at 0° C. The mixture was stirred at 60° C. for 3 hr, quenched with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure to give [2-(cyclopentylsulfonyl)phenyl]methanol (3.1 g).

Aufarbeitung

  1. customquenched with 1N hydrochloric acid
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-247ad7919d444f9f9ebcb809895a474d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481569B2

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