Trimethyltin chloride → HCID 59523083, compound

HRID 1424776Notes

Reaction equation

HRID 1424776 reaction equation
[CH2:1]([O:13][C:14]1[N:15]=[CH:16][S:17][C:18]=1[C:19]1[S:23][CH:22]=[N:21][C:20]=1[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li]CCCC.[CH3:42][Sn:43](Cl)([CH3:45])[CH3:44]>C1COCC1>[CH2:1]([O:13][C:14]1[N:15]=[C:16]([Sn:43]([CH3:45])([CH3:44])[CH3:42])[S:17][C:18]=1[C:19]1[S:23][C:22]([Sn:43]([CH3:45])([CH3:44])[CH3:42])=[N:21][C:20]=1[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 59523103HCID 59523103, compoundHCID 178418339Butyllithium

Product 1

HCID 59523083HCID 59523083, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 0.16 g (0.298 mmol) of compound 13 in 24 mL of THF was cooled to −78° C. The resulting suspension was treated dropwise with 0.29 mL (0.725 mmol) n-BuLi (2.5 M in hexanes) and stirred for 30 minutes. The dry ice bath was removed and the mixture was stirred at ambient temperature for 30 minutes. The mixture was treated with 0.167 g (0.84 mmol) of trimethyltin chloride and heated in an oil bath at 60° C. for 30 minutes. The mixture was concentrated in vacuo. The resulting oily solid was triturated with 15 mL of hexanes and filtered warm. The filtrate was concentrated in vacuo to a yellow oil that solidified on standing to give 252 mg (98% yield) of compound 14. 1H NMR (500 MHz) δ 4.46 (t, 4H, J=6.5 Hz), 1.88-1.22 (m, 40H), 0.88 (t, 6H, J=7.0 Hz), 0.44 (s, 18H).

Workup

  1. customThe dry ice bath was removed
  2. stirringthe mixture was stirred at ambient temperature for 30 minutes
  3. concentrationThe mixture was concentrated in vacuo
  4. customThe resulting oily solid was triturated with 15 mL of hexanes
  5. filtrationfiltered
  6. temperaturewarm
  7. concentrationThe filtrate was concentrated in vacuo to a yellow oil that solidified

Sources & evidence

ORD record
ord-4c5a21dd52f745a1aa12e097bec95b2b
Source dataset
uspto-grants-2015_01
Patent number
US08927971B2

Reaction notes

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