Reaktion #434497

Reaktionsgleichung

6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphtalene

THF

n-butyl lithium

→

crude oil

Ausbeute 100.0%

5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-2-naphthalenecarbaldehyde

Ausbeute 100.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA flame dried round bottom flask
2. 2
   workup.STIRRINGto stir for 30 minutes at which time it
3. 3
   Sonstigewas quenched via the addition of dimethylformamide (5.0 mL)
4. 4
   Temperaturto warm to RT where it
5. 5
   workup.STIRRINGstirred for 17 hours
6. 6
   SonstigeThe reaction was quenched by the addition of 1.0 N HCl (100 mL)
7. 7
   ExtraktionThe reaction mixture was extracted
8. 8
   SonstigeThe organics were separated
9. 9
   Trocknendried over MgSO4
10. 10
    Einengenby concentrating to dryness
11. 11
    SonstigeThe resulting oil was dried under high vacuum

Vorschrift

A flame dried round bottom flask was charged with 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphtalene (10 g, 37 mmol) and anhydrous THF (100 mL). This solution was cooled to −70° C. while stirring under a nitrogen blanket. To this solution was added 2.5 M n-butyl lithium (14.9 mL, 37 mmol). The reaction mixture was allowed to stir for 30 minutes at which time it was quenched via the addition of dimethylformamide (5.0 mL). The reaction was allowed to warm to RT where it stirred for 17 hours. The reaction was quenched by the addition of 1.0 N HCl (100 mL). The reaction mixture was extracted using ether. The organics were separated and dried over MgSO4 followed by concentrating to dryness. The resulting oil was dried under high vacuum to give a total of 8.2 g (100%) of crude oil. The product was used without further purification.

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