Tributyltin Chloride → HCID 17981611, compound

HRID 2252070Notes

Reaction equation

HRID 2252070 reaction equation
C([Li])CCC.[CH3:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1.[CH2:18]([Sn:22](Cl)([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>O1CCCC1>[CH3:6][C:7]1[S:8][C:9]([Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH3:21])=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:11]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 5843772-Methyl-4-phenyl-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 17981611HCID 17981611, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Add n-butyllithium (0.46 mL, 0.74 mmol, 1.6 M in tetrahydrofuran) to a solution of 2-methyl-4-phenylthiazole (0.13 g, 0.74 mmol) in tetrahydrofuran (7 mL) cooled to −78° C. under a nitrogen atmosphere. Stir at −78° C. for 45 minutes, add tributyltin chloride (0.2 mL, 0.74 mmol), and stir for 2 hours as the reaction mixture warms to room temperature. Add aqueous ammonium chloride and then partition the mixture between ethyl acetate and water. Extract the aqueous phase with ethyl acetate. Wash the combined organic layers sequentially with water and saturated aqueous sodium chloride, dry over sodium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with hexane containing 10% ethyl acetate to provide the desired compound in 68% yield. MS(ES+): m/z=466.1 (M+H)+

Workup

  1. stirringstir for 2 hours as the reaction mixture
  2. customwarms to room temperature
  3. customAdd aqueous ammonium chloride and then partition the mixture between ethyl acetate and water
  4. extractionExtract the aqueous phase with ethyl acetate
  5. washWash the combined organic layers sequentially with water and saturated aqueous sodium chloride
  6. dry with materialdry over sodium sulfate
  7. concentrationconcentrate under reduced pressure
  8. washeluting with hexane containing 10% ethyl acetate

Sources & evidence

ORD record
ord-c1e81babbb4d4b64ac5ed755ce1e6f5c
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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