Stannous Chloride → HCID 57567772, compound

HRID 1926174Notes

Reaction equation

HRID 1926174 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>C1COCC1.Cl.O.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 grams, 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. After addition, the mixture was stirred at room temperature for 2 hours. This colorless solution, was then added to a suspension of 2,6-dibromoanthraquinone (5.49 grams, 15.0 mmol) in dry THF (300 mL) 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. When deionized (DI) water (6.0 mL) was added, the color changed to light red, and a white precipitate appeared. Tin (II) chloride (8.088 grams, 42.6 mmol) in hydrochloric acid (HCl) (18 mL, 10 weight percent) aqueous solution was then added. The mixture was heated to 60° C. for 2 hours and then cooled to room temperature. The organic solvent was removed by rotary evaporation. Deionized (DI) water (100 mL) was added and the resulting mixture was then extracted with hexane (100 mL×3). The hexane solution was washed with DI water until neutral. The washed hexane solution was concentrated and purified by column chromatography (silica gel/hexane). A bright yellow solid (8.55 grams, yield: 82%) was obtained as the product.

Workup

  1. additionAfter addition
  2. dissolutionthe 2,6-dibromoanthraquininone dissolved in minutes
  3. stirringThe mixture was stirred at room temperature overnight
  4. additionwas added
  5. temperatureThe mixture was heated to 60° C. for 2 hours
  6. temperaturecooled to room temperature
  7. customThe organic solvent was removed by rotary evaporation
  8. additionDeionized (DI) water (100 mL) was added
  9. extractionthe resulting mixture was then extracted with hexane (100 mL×3)
  10. washThe hexane solution was washed with DI water until neutral
  11. concentrationThe washed hexane solution was concentrated
  12. custompurified by column chromatography (silica gel/hexane)

Sources & evidence

ORD record
ord-b7e096ba337a4a61a72fa55a3a9ed5e1
Source dataset
uspto-grants-2012_05
Patent number
US08178873B2

Reaction notes

Loading…