Tributyltin Chloride → HCID 11089657, compound

HRID 855122Notes

Reaction equation

HRID 855122 reaction equation
C([Li])CCC.[CH2:6]([O:8][C:9]#[CH:10])[CH3:7].[CH2:11]([Sn:15](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>C(OCC)C>[CH2:20]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[C:10]#[C:9][O:8][CH2:6][CH3:7])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 61239Ether, ethyl ethynylHCID 178418339Butyllithium

Product 1

HCID 11089657HCID 11089657, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-35 °C

Procedure

A solution of n-butyllithium (18.7 mL-1.6 M in hexanes, 30.0 mmole) was added to anhydrous ethyl ether (20 mL) and the resulting mixture was then cooled to −30 to −40 ° C. A solution of ethoxy acetylene (5.00 g-40% in hexanes, 28.5 mmole) in ethyl ether (10 mL) was then added dropwise over 10 minutes. The resulting suspension was allowed to warm to room temperature, tributyltin chloride (9.29 g, 28.5 mmole) was added dropwise over 10 minutes and the mixture was stirred for 2 hrs. The mixture was filtered through a celite pad, washed with ethyl ether and concentrated in vacuo to give an assumed quantitative yield of the crude product as a red oil: 1H NMR (dmso-d6/300 MHz) 4.04 (q, 2H, J=7.05 Hz), 1.54-1.44 (m, 6H), 1.34-1.21 (m, 12H), 0.96-0.78 (m, 15H).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe mixture was filtered through a celite pad
  3. washwashed with ethyl ether
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c30e924b32ea4bc99232f92ef2cf9ce5
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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