Reaktion #159528

Reaktionsgleichung

acetic acid

n-Butyllithium

N-tert-Butylmethanesulfonamide

Methyl 4-fluorobenzoate

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product

Ausbeute 36.6%

N-(tert-Butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide

Ausbeute 36.6%

Lösungsmittel

ethyl acetate

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Temperaturcooled again to −78° C
3. 3
   Temperaturcooled
4. 4
   SonstigeThe solution prepared
5. 5
   workup.ADDITIONabove was added dropwise at low temperature
6. 6
   workup.ADDITIONAfter the addition
7. 7
   Sonstigeto come to room temperature
8. 8
   workup.STIRRINGstirred for a further 1 hour
9. 9
   Waschenthe mixture was washed with saturated sodium hydrogencarbonate solution (50 ml) and saturated sodium chloride solution (50 ml)
10. 10
    TrocknenThe organic phase was dried over magnesium sulfate
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated by rotary evaporation
13. 13
    SonstigePurification
14. 14
    Einengenconcentrated by rotary evaporation
15. 15
    Sonstigedried under reduced pressure

Vorschrift

N-tert-Butylmethanesulfonamide (1.00 g) was initially charged in THF (10 ml) and cooled to −78° C. n-Butyllithium (1.6 N in hexane, 9.00 ml) was added dropwise. Subsequently, the mixture was warmed up to 0° C. within 5 minutes, stirred for 5 further minutes and cooled again to −78° C. Methyl 4-fluorobenzoate (1.56 g) in THF (10 ml) dissolved and to −78° C. cooled. The solution prepared above was added dropwise at low temperature. After the addition had ended, the mixture was allowed to come to room temperature and stirred for a further 1 hour. After the addition of acetic acid (0.82 ml) and ethyl acetate (50 ml), the mixture was washed with saturated sodium hydrogencarbonate solution (50 ml) and saturated sodium chloride solution (50 ml). The organic phase was dried over magnesium sulfate, filtered and concentrated by rotary evaporation. Purification was effected via normal phase with an n-heptane/ethyl acetate gradient. The fractions of value were combined, concentrated by rotary evaporation and dried under reduced pressure. This gave the product (661 mg) with a molecular weight of 273.3 g/mol (C12H16FNO3S), MS (EST): m/e=296 (M+Na+).

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