反応 #60358

反応方程式

(6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester

n-Butyllithium

DMF

→

title compound

(6-formyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added drop-wise to the stirred solution
2. 2
   温度the mixture was slowly warmed to RT overnight
3. 3
   その他The reaction was quenched with saturated aqueous NH4Cl solution
4. 4
   抽出extracted with EtOAc
5. 5
   乾燥The combined organics were dried over MgSO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to afford the crude material, which
8. 8
   その他was purified by flash column chromatography

実験手順

(6-Bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (Step C) (1.080 g, 3.311 mmol) was dissolved in THF (30 mL) and cooled to −78° C. n-Butyllithium (2.5 M) (3.311 mL, 8.276 mmol) was added drop-wise to the stirred solution. The reaction was stirred at −78° C. for 30 min and DMF (1.282 mL, 16.55 mmol) was added drop-wise and the mixture was slowly warmed to RT overnight. The reaction was quenched with saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organics were dried over MgSO4 and concentrated in vacuo to afford the crude material, which was purified by flash column chromatography to furnish the pure title compound. MS (APCI pos) 217 (M-t-Bu).

出典