Trimethyltin chloride → HCID 58434863, compound

HRID 1424771Notes

Reaction equation

HRID 1424771 reaction equation
[CH2:1]([O:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]1[S:20][CH:21]=[CH:22][C:23]=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.C(OCC)(=O)C>[CH3:42][Sn:43]([CH3:45])([CH3:44])[C:17]1[S:16][C:15]([C:19]2[S:20][C:21]([Sn:43]([CH3:45])([CH3:44])[CH3:42])=[CH:22][C:23]=2[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])=[C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:18]=1

Participants

6

Reactant 3

HCID 14016Trimethyltin chlorideHCID 68513081HCID 68513081, compoundHCID 178418339Butyllithium

Product 1

HCID 58434863HCID 58434863, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2.9 g (5.42 mmol) of 3,3′-didodecyloxy-2,2′-bithiophene (Org. Lett. 2008, 10, 5333) in 150 mL of THF was cooled to −78° C. The resulting suspension was treated dropwise with 5.2 mL (13.0 mmol) of n-BuLi (2.5 M in hexanes) and stirred for an additional 45 minutes. The dry ice bath was then removed and the mixture was stirred at ambient temperature for 1.25 hours. The suspension was cooled to −78° C. and treated with a solution of 3.02 g (15.2 mmol) of trimethyltin chloride in 15 mL of THF. The mixture was stirred for 90 minutes at ambient temperature. The mixture was diluted with 100 mL of ethyl acetate and washed successively with 50 mL of water and 50 mL of brine. The separated organic layer was dried over K2CO3, filtered, and concentrated in vacuo. The resulting solid was recrystallized from cold pentane to give 3.8 g (81% yield) of 5,5′-bis(trimethylstannyl)-3,3′-bis(dodecyloxy)2,2′-bithiophene as light tan needles. m.p. 66-67° C. 1H NMR (500 MHz) δ 6.88 (s, 2H), 4.11 (t, 4H, J=6.4 Hz), 1.84 (m, 4H), 1.55-1.30 (m, 36H), 0.88 (m, 6H), 0.36 (s, 18H).

Workup

  1. customThe dry ice bath was then removed
  2. stirringthe mixture was stirred at ambient temperature for 1.25 hours
  3. stirringThe mixture was stirred for 90 minutes at ambient temperature
  4. washwashed successively with 50 mL of water and 50 mL of brine
  5. dry with materialThe separated organic layer was dried over K2CO3
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting solid was recrystallized from cold pentane

Sources & evidence

ORD record
ord-c2f858843e0243b28a5c1e3605b2a293
Source dataset
uspto-grants-2015_01
Patent number
US08927971B2

Reaction notes

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