Reaktion #60358

Reaktionsgleichung

(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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added drop-wise to the stirred solution
2. 2
   Temperaturthe mixture was slowly warmed to RT overnight
3. 3
   SonstigeThe reaction was quenched with saturated aqueous NH4Cl solution
4. 4
   Extraktionextracted with EtOAc
5. 5
   TrocknenThe combined organics were dried over MgSO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto afford the crude material, which
8. 8
   Sonstigewas purified by flash column chromatography

Vorschrift

(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).

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