Reaktion #78288

Reaktionsgleichung

NaOH

Lithium borohydride

ester

1-Thiophen-2-yl-methylcyclobutanecarboxylic acid ethyl ester

MeOH

→

(1-Thiophen-2-yl-methylcyclobutyl)methanol

Lösungsmittel

Et2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   Sonstigecontinued at 0° C. until effervescence
3. 3
   workup.STIRRINGto stir an additional hour, at which time the mixture
4. 4
   workup.STIRRINGstirred an additional 0.5 h
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed with brine
7. 7
   Trocknendried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigeThe crude alcohol 4 was purified by FCC (silica gel, 1:1 hexane/CH2Cl2)

Vorschrift

Lithium borohydride (435 mg, 20 mmol) was added to a solution of ester 3 (2.3 g, 10 mmol) in Et2O (20 mL) at 0° C. After having stirred for 5 min, MeOH (640 mg, 20 mmol) was added dropwise and stirring continued at 0° C. until effervescence ceased. The mixture was warmed to 23° C. and was allowed to stir an additional hour, at which time the mixture was poured into 3N NaOH and stirred an additional 0.5 h. The organic layer was separated and washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude alcohol 4 was purified by FCC (silica gel, 1:1 hexane/CH2Cl2).

Quelle