Tributyltin Chloride → HCID 22609752, compound

HRID 2306701Notes

Reaction equation

HRID 2306701 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)[CH3:3].[Li]CCCC.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>C1COCC1>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:3]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 178703303-(1H-Imidazol-1-yl)-N,N-dimethylpropan-1-amineHCID 178418339Butyllithium

Product 1

HCID 22609752HCID 22609752, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1-(N,N-Dimethylaminopropyl) imidazole (2 g) in THF (20 ml) at −78° C. was treated with nBuLi (8.6 ml, 1.6 M) under nitrogen. After 30 minutes at −78° C., tri-n-butylstannyl chloride was added and the mixture allowed to warm to 20° C. The mixture was concentrated in vacuo, taken up in n-hexane and filtered. The filtrate was concentrated in vacuo to give the title compound (4.33 g) as a yellow oil; δH CDCl3 7.28 (1H, s), 7.09 (1H, s), 3.97 (2H, t), 2.25 (2H, t), 2.20(6H, s), 1.90 (2H, m) 1.55 (6H, m), 1.34 (12H, m), 0.92 (9H, m).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-118504f876464da18b9760820c0e879e
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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