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Chemical Structure| 132170-05-9

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Product Details of [ 132170-05-9 ]

CAS No. :132170-05-9
Formula : C14H24Si2
M.W : 248.51
SMILES Code : C[Si](C1=C2CCC2=C([Si](C)(C)C)C=C1)(C)C
MDL No. :MFCD31651480

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Application In Synthesis of [ 132170-05-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 132170-05-9 ]

[ 132170-05-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 75-77-4 ]
  • [ 694-87-1 ]
  • [ 132170-05-9 ]
YieldReaction ConditionsOperation in experiment
Example 15, Step aLithium (0.533 g, 77 mmol) was taken in a 50 mL three necked round-bottom flask, added THF (20 mL) at 0 °C and stirred vigorously. TMSC1 (7.36 mL, 57.6 mmol) was added to the reaction mixture followed by drop-wise addition of 1,2- dihydrocyclobutabenzene (2 g, 19.20 mmol). The reaction mixture was stirred at room temperature for 6 days. The reaction mixture was syringed out from the unreacted lithium and then the reaction mixture was quenched with MeOH (10 mL) at 0 °C. Water (25 mL) was added and the resulting solution was extracted with petroleum ether (3 x 40 mL). The combined organic layer was washed with brine (25 mL), dried over Na2S04, and concentrated at 25 °C to yield a mixture of crude dienes (4.6 g) as yellow oil. GC/MS (Condition 16): Rt = 6.95 min., GC/MS: Anal. Calcd. for [M]+ Ci4H26Si2: 250.16; found 250.2.The mixture of crude dienes (7.0 g, 27.9 mmol) was dissolved in THF (50 mL) and heated to 40 °C. A solution of DDQ (3.17 g, 13.97 mmol) in THF (20 mL) was added drop-wise to the reaction mixture and heated at the same temperature further for 1 h. Water (100 mL) was added to the reaction mixture and extracted with EtOAc (4 x 50 mL). The organic layer was washed successively with water (100 mL), saturated a2C03 (150 mL), brine (50 mL), dried over Na2S04 and concentrated under reduced pressure at 25 °C to yield crude 3,6-bis(trimethylsilyl)-l,2- dihydrocyclobutabenzene (7.9 g). GC/MS (Condition 16): Rt = 7.60 min. GC/MS: Anal. Calcd. for [M]+ Ci4H24Si2: 248.14; found 248.0. A solution of Br2 (4.66 mL, 91 mmol) in MeOH ( 20 mL) was added drop- wise to a solution of crude 3,6-bis(trimethylsilyl)-l,2-dihydrocyclobutabenzene (7.5 g, 30.2 mmol) in MeOH (75 mL) at 0 °C and stirred at 25 °C for overnight.Water (100 mL) was added to the reaction mixture and extracted with petroleum ether (3 x 100 mL). The combined organic layer was washed with brine (50 mL), dried over Na2S04 and concentrated under reduced pressure at 25 °C. The crude was purified by Combiflash Isco (Silicycle, 120 g, silica, 100percent petroleum ether) to yield dibromide 15a (3.9 g). GC/MS (Condition 16): Rt = 7.07 min. XH NMR (CDC13, delta = 7.26 ppm, 400 MHz): delta 7.17 (s, 2H), 3.09 (s, 4H). GC/MS: Anal. Calcd. for [M]+ C8H6Br2: 261.94; found 261.9.
 

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