Реакция #462050

Уравнение реакции

hexamethylphosphoramide

N-Butyllithium

6-bromo-2-naphthol

N,N-dimethylformamide

tertbutyllithium

→

solid

Выход 81.0%

6-Hydroxy-2-naphthaldehyde

Выход 81.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred for 30 min at -78° C
2. 2
   Другоеtwo hours
3. 3
   Другоеat -20° C
4. 4
   workup.STIRRINGAfter stirring for 20 minutes
5. 5
   Другоеto come to room temperature
6. 6
   workup.STIRRINGstirred for 1 hour
7. 7
   Другоеquenched with aqueous ammonium chloride
8. 8
   workup.ADDITIONThe mixture was poured into water
9. 9
   Экстракцияextracted with EtOAc
10. 10
    СушкаThe organic extracts were dried over MgSO4
11. 11
    ДругоеEvaporation and purification by flash chromatography (hexane/EtOAc 3/1 )

Методика

Step a) N-Butyllithium (35.9 mL, 89.7 mmol) was added dropwise to a cold (-78° C.) solution of 6-bromo-2-naphthol (20.0 g, 89.7 mmol) in THF (200 mL). After stirring for 10 minutes, tertbutyllithium (52.76 mL, 89.7 mmol) was added dropwise. The mixture was stirred for 30 min at -78° C, and two hours at -20° C. Then, hexamethylphosphoramide (15.6 mL, 89.7 mmol) was added to the reaction mixture. After stirring for 20 minutes. N,N-dimethylformamide (6.94 mL, 89.7 mmol) was added dropwise. The mixture was allowed to come to room temperature, stirred for 1 hour, and quenched with aqueous ammonium chloride. The mixture was poured into water, acidified with 2N HCL and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexane/EtOAc 3/1 ), gave a yellow solid (12.5 g, 81% yield, m.p. 173°-174 ° C.).

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