Tributyltin Chloride → HCID 71143866, compound

HRID 2173013Notes

Reaction equation

HRID 2173013 reaction equation
[F:1][CH:2]([F:8])[C:3]1[CH:7]=[CH:6][S:5][N:4]=1.C([Li])CCC.[CH2:14]([Sn:18]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])Cl)[CH2:15][CH2:16][CH3:17].C([O-])(O)=O.[Na+]>C1COCC1>[F:1][CH:2]([F:8])[C:3]1[CH:7]=[C:6]([Sn:18]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:14][CH2:15][CH2:16][CH3:17])[S:5][N:4]=1

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 54118089HCID 54118089, compoundHCID 178418339Butyllithium

Product 1

HCID 71143866HCID 71143866, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of 3-(difluoromethyl)isothiazole (93 mg, 0.688 mmol) in anhydrous THF (2.0 mL) was added n-butyllithium (0.473 mL, 0.757 mmol) dropwise. The reaction mixture was stirred for 60 minutes at −78° C. A solution of tributylchlorostannane (0.223 mL, 0.826 mmol) in anhydrous THF (0.5 mL) was added and the reaction mixture was stirred for 30 minutes at −78° C. The solution was subsequently allowed to warm to room temperature over a period of about one hour. Saturated aq NaHCO3 was added, and the aqueous phase was extracted with EtOAc. The organic phases were combined, dried over anhydrous sodium sulfate, passed through a short pad of silica gel (eluting with EtOAc) and evaporated in vacuo to give the title compound, which was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 30 minutes at −78° C
  2. temperatureto warm to room temperature over a period of about one hour
  3. extractionthe aqueous phase was extracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-487d99538f23424f88fe71ddea59838e
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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