Stannous Chloride → HCID 57567772, compound

HRID 1727842Notes

Reaction equation

HRID 1727842 reaction equation
[CH:1]([Si:4]([C:11]#[CH:12])([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C([Li])[CH2:14][CH2:15][CH3:16].[Br:18][C:19]1[CH:32]=[CH:31][C:30]2[C:29](=O)[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([Br:34])[CH:27]=3)[C:22](=O)[C:21]=2[CH:20]=1.[Sn](Cl)Cl>Cl.O.C1COCC1.CCCCCC>[Br:18][C:19]1[CH:32]=[CH:31][C:30]2[C:21](=[C:22]([C:2]#[C:1][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:15]([CH3:16])[CH3:14])[CH:5]([CH3:7])[CH3:6])[C:23]3[C:28]([C:29]=2[C:12]#[C:11][Si:4]([CH:5]([CH3:6])[CH3:7])([CH:1]([CH3:3])[CH3:2])[CH:8]([CH3:10])[CH3:9])=[CH:27][C:26]([Br:34])=[CH:25][CH:24]=3)[CH:20]=1

Participants

9

Reactant 4

HCID 24479Stannous ChlorideHCID 2734682(Triisopropylsilyl)acetyleneHCID 109594842,6-DibromoanthraquinoneHCID 178418339Butyllithium

Product 1

HCID 57567772HCID 57567772, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Triisopropylsilylacetylene (12.32 g, 67.5 mmol) and dry hexane (140 mL) were added under a dry nitrogen blanket to an oven-dried round bottom flask (1 L). Butyl lithium (2.7 M in hexane, 14.5 mL, 39.2 mmol) was added dropwise under dry nitrogen through a syringe to the mixture. The mixture was stirred at room temperature for 2 hours. To this colorless solution, dry THF (300 mL) and 2,6-dibromoanthraquinone (5.49 g, 15.0 mmol) were added under dry nitrogen. The solution turned red immediately and the 2,6-dibromoanthraquininone dissolved in minutes. The mixture was stirred at room temperature overnight and the solution became dark red. Deionized (DI) water (6.0 mL) was added, the color changed to light red, and a white precipitate appeared. Tin (II) chloride (8.088 g, 42.6 mmol) in HCl (18 mL, 10%) aqueous solution was then added. The mixture was heated to 60° C. for 2 hours and then cooled to room temperature. The solvent was removed by rotary evaporation. DI water (100 mL) was added to the mixture which was then extracted with hexane (100 mL×3). The hexane solution was washed with DI water until neutral. It was concentrated and purified through a column chromatography (silica gel/hexane, Rf=0.7). A bright yellow solid (8.55 g, yield: 82%) was obtained as the product. 1H NMR (400 MHz, CDCl3). δ ppm 8.797-8.802 (d, 2H, J=2.0 Hz), 8.431-8.454 (d, 2H, J=8.8 Hz), 7.647-7.674 (dd, 2H, J=8.8 Hz, J=2.0 Hz), 1.259 (s, 36H), 1.247 (s, 6H).

Workup

  1. dissolutionthe 2,6-dibromoanthraquininone dissolved in minutes
  2. stirringThe mixture was stirred at room temperature overnight
  3. temperatureThe mixture was heated to 60° C. for 2 hours
  4. temperaturecooled to room temperature
  5. customThe solvent was removed by rotary evaporation
  6. additionDI water (100 mL) was added to the mixture which
  7. extractionwas then extracted with hexane (100 mL×3)
  8. washThe hexane solution was washed with DI water until neutral
  9. concentrationIt was concentrated
  10. custompurified through a column chromatography (silica gel/hexane, Rf=0.7)

Sources & evidence

ORD record
ord-14f35374962a47b7a854aafa418325b8
Source dataset
uspto-grants-2009_02
Patent number
US07495251B2

Reaction notes

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