Reaktion #68541

ord-943bb78d112d4fcaa64625a57cd98ea3

Reaktionsgleichung

[Li][CH2]CCC
Butyllithium
Cc1nccs1
2-methylthiazole
[CH3][Sn]([CH3])([CH3])[Cl]
Chlorotrimethylstannane
Cc1nc[c]([Sn]([CH3])([CH3])[CH3])s1
2-methyl-5-(trimethylstannyl)thiazole

Lösungsmittel

Reaktionsbedingungen

Temperatur
-78°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGStirring
  2. 2
    workup.WAITwas continued at −78° C. for 45 min
  3. 3
    SonstigeThe reaction mixture was quenched with a satured aqueous solution of NaHCO3
  4. 4
    ExtraktionThe aqueous layer was extracted with Et2O
  5. 5
    TrocknenThe organic extracts were dried over MgSO4
  6. 6
    Filtrationfiltered
  7. 7
    Einengenconcentrated in vacuo
  8. 8
    SonstigeUsed in the next step without purification (obtained 1.29 g)

Vorschrift

Butyllithium (1.6M in THF, 3.5 ml, 5.5 mmol) was added to a stirred solution of 2-methylthiazole (0.45 ml, 5.0 mmol) in THF (15 mL) at −78° C. The reaction mixture was stirred at −78° C. for 40 min. Chlorotrimethylstannane (1M in THF, 5.0 ml, 5.0 mmol) was added. Stirring was continued at −78° C. for 45 min. The reaction mixture was quenched with a satured aqueous solution of NaHCO3. The aqueous layer was extracted with Et2O. The organic extracts were dried over MgSO4, filtered and concentrated in vacuo. Used in the next step without purification (obtained 1.29 g). MS m/z=264.1. Calc'd for C7H13NSSn: 261.94.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524900B2uspto-grants-2013_09