Pentane → Tri-t-butyltin chloride

HRID 66781Notes

Reaction equation

HRID 66781 reaction equation
[C:1]([Sn:5]([Cl:11])(F)[C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2].CCCCC.[C:17]([Li])([CH3:20])([CH3:19])[CH3:18]>CCCCCCC>[C:1]([Sn:5]([Cl:11])([C:17]([CH3:20])([CH3:19])[CH3:18])[C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8003PentaneHCID 13041092Di-t-butyltin chloride fluorideHCID 178418306HCID 178418306, compound

Product 1

HCID 13041090Tri-t-butyltin chloride

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of di-t-butyltin chloride fluoride (5.0 g., 0.017 mole) in heptane (100 ml.) was cooled to -78° C., and a pentane solution of t-butyl-lithium (20 ml., 1.95 M) was added dropwise. After the addition was completed, stirring was continued for 2 hrs., the cooling bath was removed, and the mixture was allowed to warm to room temperature with stirring for 6 more hrs. The resulting pale yellow mixture was worked up to give a thick, pale yellow oil which was chromatographed with pentane. Evaporation of the solvent left a clear oil which solidified spontaneously (5.0 g., 88.3%), m.p. 31-32; (b.p. 122°-123°/5 mm. (Found: C, 44.15; H, 8.15; Cl, 10.95. C12H27ClSn requires C, 44.3; H, 8.35; Cl, 10.9%); n.m.r. 61.35 (s).

Workup

  1. additionAfter the addition
  2. custom, the cooling bath was removed
  3. temperatureto warm to room temperature
  4. stirringwith stirring for 6 more hrs
  5. customto give a thick, pale yellow oil which
  6. customwas chromatographed with pentane
  7. customEvaporation of the solvent
  8. waitleft a clear oil which

Sources & evidence

ORD record
ord-58787eb88f584aba816d3bd999456949
Source dataset
uspto-grants-1982_08
Patent number
US04343815

Reaction notes

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