Water → HCID 44203211, compound

HRID 929271Notes

Reaction equation

HRID 929271 reaction equation
[CH2:1]([C:13]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:23]2[CH:22]=[CH:21][S:20][C:19]=2[C:15]2[S:16][CH:17]=[CH:18][C:14]1=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([Li])(C)(C)C.[CH3:41][Sn:42](Cl)([CH3:44])[CH3:43].O>C1COCC1.CCCCC>[CH2:24]([C:13]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:14]2[CH:18]=[C:17]([Sn:42]([CH3:44])([CH3:43])[CH3:41])[S:16][C:15]=2[C:19]2[S:20][C:21]([Sn:42]([CH3:44])([CH3:43])[CH3:41])=[CH:22][C:23]1=2)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 44203214HCID 44203214, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 44203211HCID 44203211, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A dry three-neck round bottom flask was equipped with a Schlenk adapter, dropping funnel, and rubber septum. Under nitrogen, 4,4-didodecyl-4H-cyclopenta[1,2-b:5,4-b′]dithiophene (0.51 g, 1 mmol) was dissolved in dry THF (12 ml) and cooled −78° C. using a dry ice/acetone cold bath. Under nitrogen, a solution of t-butyllithium (1.7 M in pentane, 2.35 ml, 4 mmol) was added dropwise over 15 minutes to the reaction vessel. The reaction was stirred at −78° C. under nitrogen for one hour and stirred at room temperature for 3 hours. Under nitrogen, a solution of trimethyltin chloride (1.0 g, 5 mmol) in dry pentane (2 ml) was added dropwise over 5 minutes to the reaction vessel at −78° C. The reaction was stirred at −78° C. under nitrogen for 1 hour and subsequently warmed to room temperature and stirred overnight. The mixture was then poured into deionized water (3×100 ml) and the organic phase extracted with hexanes (3×50 ml). The organic phases were collected and washed with deionized water (3×50 ml), dried over sodium sulphate, filtered, and concentrated. The product was dried under high vacuum with agitation for 48 hours to give 0.80 g of product as colorless oil, yield 95%. 1H NMR (500 MHz, CD2Cl2) δ (ppm): 6.94 (s, 2H), 1.79-1.76 (m, 4H), 1.29-1.15 (m, 36H), 1.08-1.02 (m, 4H), 0.88 (t, J=6.0 Hz, 6H), 0.39 (s, 18H).

Workup

  1. customA dry three-neck round bottom flask was equipped with a Schlenk adapter
  2. stirringstirred at room temperature for 3 hours
  3. stirringThe reaction was stirred at −78° C. under nitrogen for 1 hour
  4. temperaturesubsequently warmed to room temperature
  5. stirringstirred overnight
  6. extractionthe organic phase extracted with hexanes (3×50 ml)
  7. customThe organic phases were collected
  8. washwashed with deionized water (3×50 ml)
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe product was dried under high vacuum with agitation for 48 hours

Sources & evidence

ORD record
ord-9fc7f22376d34b47b58ffb55af13b06f
Source dataset
uspto-grants-2016_03
Patent number
US09293708B2

Reaction notes

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