反応 #78288

反応方程式

NaOH

Lithium borohydride

ester

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

MeOH

→

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

溶媒

Et2O

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   その他continued 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
   その他The organic layer was separated
6. 6
   洗浄washed with brine
7. 7
   乾燥dried (Na2SO4)
8. 8
   ろ過filtered
9. 9
   濃縮concentrated in vacuo
10. 10
    その他The crude alcohol 4 was purified by FCC (silica gel, 1:1 hexane/CH2Cl2)

実験手順

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).

出典