Tributyltin Chloride → HCID 22731088, compound

HRID 2085372Notes

Reaction equation

HRID 2085372 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[O:5][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:7][N:8]=1.C([Li])CCC.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22]>C1COCC1.CCCCCC>[CH2:28]([Sn:23]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:24][CH2:25][CH2:26][CH3:27])[C:2]#[C:3][C:4]1[O:5][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:7][N:8]=1)[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 22731093HCID 22731093, compoundHCID 178418339Butyllithium

Product 1

HCID 22731088HCID 22731088, compoundYield 109.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of 1,1-dibromo-2-(5-t-butyl-oxazol-2-yl)ethylene (6.0 g, 19 mmole) in anhydrous THF (80 mL) at −78 deg C. under argon atmosphere. was added with 1.6 M n-butyllithium (32 mL, 51 mmole) in hexane dropwise over 20 min., the reaction mixture, stirred at −78 deg C. for 30 min and treated with tributyltin chloride (5.5 mL, 20 mmole). The reaction mixture was stirred for 30 min, warmed to 0 deg C., stirred at 0 deg C. for 30 min, and then at room temperature for 45 min. The mixture was passed through a short column of silica gel (deactivated with 2% triethylamine in hexane), and eluted with 10% EtOAc in dichloromethane to obtain crude product of 1-tributylstannyl-2-(5-t-butyl-oxazol-2-yl)acetylene as a brown oil (9.10 g).

Workup

  1. customat −78 deg C
  2. stirringThe reaction mixture was stirred for 30 min
  3. temperaturewarmed to 0 deg C
  4. stirring, stirred at 0 deg C
  5. waitfor 30 min
  6. waitat room temperature for 45 min
  7. washeluted with 10% EtOAc in dichloromethane

Sources & evidence

ORD record
ord-6e35464f1ed445c99c029715a8c9f460
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

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