Tributyltin Chloride → HCID 57516642, compound

HRID 1898608Notes

Reaction equation

HRID 1898608 reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][CH2:11][CH2:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Li]CCCC.[CH2:18]([Sn:22]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:24][CH2:25][CH2:26][CH3:27])Cl)[CH2:19][CH2:20][CH3:21]>C1COCC1>[C:8]1([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Sn:22]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=2)[CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 57516641HCID 57516641, compoundHCID 178418339Butyllithium

Product 1

HCID 57516642HCID 57516642, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-iodo-4-cyclopent-1-enyl-pyridine (150 mg, 0.55 mmol) in THF (3 mL) at −78° C. was added n-BuLi (1.6 M in hexanes, 0.38 mL, 0.61 mmol). The resulting deep orange-brown solution was stirred at −78° C. for 15 min then tributylchlorostannane (0.17 mL, 61 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 30 min then warmed to room temperature over 30 min, quenched with water and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated to provide 4-cyclopent-1-enyl-2-tributylstannanyl-pyridine as an orange oil which was used without further purification.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 30 min
  2. temperaturethen warmed to room temperature over 30 min
  3. customquenched with water
  4. extractionextracted with EtOAc (2×)
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-35c5fb144bd44b418f28da0f80e8d234
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…