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Chemical Structure| 232-55-3 Chemical Structure| 232-55-3

Structure of 232-55-3

Chemical Structure| 232-55-3

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Product Details of [ 232-55-3 ]

CAS No. :232-55-3
Formula : C13H10
M.W : 166.22
SMILES Code : C12=C(CC=C2)C=CC3=CC=CC=C13
English Name :3H-Benz[E]Indene
MDL No. :MFCD06797439

Safety of [ 232-55-3 ]

Application In Synthesis of [ 232-55-3 ]

* 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 [ 232-55-3 ]

[ 232-55-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 6342-87-6 ]
  • [ 232-55-3 ]
YieldReaction ConditionsOperation in experiment
85.1% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; 3H-cyclopenta[a]naphthalene (6). In a drybox, LiAlH4 (2.92 g, 76.9 mmol, 0.499 equiv) was weighed into a 500 mL round bottom ask equipped with a magnetic stirbar. Upon removal from the drybox, 308 mL of THF was added, and the resulting gray suspension was cooled to 0 C. Under a stream of nitrogen, ketone 7 (28.05 g, 154 mmol, 1.00 equiv) was added in a single portion. The reaction mixture was warmed to room temperature, stirred for an additional 1.5 hours, then re-cooled to 0 C. H2O was added dropwise until no further evolution of hydrogen gas was apparent. Aqueous 1 N HCl (385 mL, 385 mmol, 2.50 equiv) was then added, and the biphasic reaction mixture was brought to reux and stirred vigorously for 12 hours. The reaction mixture was transferred to a separatory funnel and the product was extracted with Et2O (3 x 500 mL). The combined organics were washed with saturated NaCl (1000 mL), dried over Na2SO4,ltered,and concentrated to aord a crude yellow oil. The crude oil was ltered through a plug of silica with hexanes as the eluant to aord the desired product as a white crystalline solid (21.8 g, 85.1%),
77% Stage #1: 2,3-dihydro-1H-benz<e>indene-1-one With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; Stage #2: With toluene-4-sulfonic acid In toluene for 0.166667h; Dean-Stark; Reflux; 3H-Cyclopenta[a]naphthalene To a solution of 105.0 g (0.58 mol) of 2,3-dihydro-1 /-/-cyclopenta[a]naphthalen-1 -one in 600 ml of THF 18.55 g of NaBH4 was added in one portion. Then, to this mixture cooled to 0°C 300 ml of methanol was added dropwise for 2 h. The resulting mixture was stirred overnight at room temperature and then evaporated to dryness. After that 0.5 M HCI was added to the residue, and the obtained mixture was thoroughly shaken. Then, the mixture was extracted with 3 χ 300 ml of dichloromethane. The combined organic extract was dried over Na2S04 and then evaporated to dryness. The residue was dissolved in 200 ml of toluene, and the obtained solution was evaporated again. Finally, to the residue dissolved in 600 ml of toluene 0.75 g of TsOH was added. The obtained solution was refluxed with Dean-Stark trap for 10 min, cooled to room temperature, and then passed through a short layer of silica gel 60 (40-63 urn). The filtrate was evaporated to dryness, and crude product was isolated from the residue by flash chromatography using 400 ml of silica gel 60 (40-63 urn) and hexane as eluent to give -75 g of the greenish viscous oil. This oil was distilled in vacuum to give 74.23 g (77%) of the title product as a colorless crystalline solid, b.p. 145- 155°C/7 mm Hg. Anal. calc. for Ci3Hi0: C, 93.94; H, 6.06. Found: C, 93.86; H, 6.19.
Multi-step reaction with 2 steps 1: LiAlH4 2: oxalic acid
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C 2: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 12 h / Reflux

 

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