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[ CAS No. 13683-41-5 ] {[proInfo.proName]}

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Chemical Structure| 13683-41-5
Chemical Structure| 13683-41-5
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Product Details of [ 13683-41-5 ]

CAS No. :13683-41-5 MDL No. :MFCD00014927
Formula : C5H11BrSi Boiling Point : -
Linear Structure Formula :- InChI Key :VVDJVCJVVHHCIB-UHFFFAOYSA-N
M.W : 179.13 Pubchem ID :83660
Synonyms :

Safety of [ 13683-41-5 ]

Signal Word:Danger Class:3
Precautionary Statements:P210 UN#:1993
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 13683-41-5 ]

* 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 [ 13683-41-5 ]

[ 13683-41-5 ] Synthesis Path-Downstream   1~84

  • 2
  • [ 13683-41-5 ]
  • [ 100-52-7 ]
  • [ 51666-96-7 ]
YieldReaction ConditionsOperation in experiment
(i) tBuLi, THF, (ii) /BRN= 471223/; Multistep reaction;
(i) tBuLi, Et2O, pentane, (ii) /BRN= 471223/; Multistep reaction;
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In tetrahydrofuran at 20℃; Heating; Stage #2: benzaldehyde In tetrahydrofuran at 0 - 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran
  • 3
  • [ 75-21-8 ]
  • [ 13683-41-5 ]
  • [ 86486-85-3 ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium; ethylene dibromide In tetrahydrofuran at 40℃; for 1h; Inert atmosphere; Stage #2: oxirane With copper(l) iodide In tetrahydrofuran at -78 - 20℃; for 3.5h; 31.1 Step 1: 3-Trimethylsilylbut-3-en-l-ol l-Bromovinyl(trimethyl) silane (14.7 mL, 87.42 mmol) was added dropwise to magnesium (3.35 g, 137.14 mmol) in tetrahydrofuran (45 mL) at 40 °C under nitrogen. Simultaneously, l,2-dibromoethane (0.3 mL) was added to initiate the reaction. On completion of the addition, the mixture was stirred for 1 h at 40 °C before it was allowed to cool to room temperature and more tetrahydrofuran (150 mL) was added. The mixture was then added slowly to a suspension of copper iodide (17.45 g, 91.17 mmol) in tetrahydrofuran (100 mL) at -78 °C. After the mixture had been allowed to warm to - 30 °C, it was stirred for 30 min and then a solution of oxirane (22 mL, 436.08 mmol) in tetrahydrofuran (35 mL), cooled to - 78 °C, was added. The temperature of the reaction mixture was maintained at -30 °C for 2 hours, before being allowed to rise to room temperature at which temperature it was stirred for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (150 mL) and water (150 mL), the latter then being extracted with MTBE (3 x 150 mL). The combined organic extracts were dried over sodium sulfate and evaporated. The residue was purified by silica-gel column chromatography on a 330 g column, eluting from 0% to 15% of MTBE in heptane to provide 3-trimethylsilylbut-3-en-l-ol (8.62 g, 68%) as a yellowish oil. 'H NMR (400 MHz, CDCb) d 5.69 - 5.65 (m, 1H), 5.48 (d, J = 2.9 Hz, 1H), 3.69 (q, J = 6.4 Hz, 2H), 2.44 (t, J = 6.6 Hz, 2H), 1.44 (br. s., 1H), 0.15 - 0.08 (m, 9H). ESI-MS m/z calc. 144.097, found 145.2 (M+l)+; Retention time: 1.723 minutes (LC method E).
68% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium; ethylene dibromide In tetrahydrofuran at 40℃; for 1h; Inert atmosphere; Stage #2: oxirane With copper(l) iodide In tetrahydrofuran at -78 - 20℃; for 3.5h; 16.1 Step 1: 3-Trimethylsilylbut-3-en-l-ol l-Bromovinyl(trimethyl)silane (14.7 mL, 87.42 mmol) was added dropwise to magnesium (3.35 g, 137.14 mmol) in tetrahydrofuran (45 mL) at 40 °C under nitrogen. Simultaneously, l,2-dibromoethane (0.3 mL) was added to initiate the reaction. On completion of the addition, the mixture was stirred for 1 h at 40 °C before it was allowed to cool to room temperature and more tetrahydrofuran (150 mL) was added. The mixture was then added slowly to a suspension of copper iodide (17.45 g, 91.17 mmol) in tetrahydrofuran (100 mL) at -78 °C. After the mixture had been allowed to warm to - 30 °C, it was stirred for 30 min and then a solution of oxirane (22 mL, 436.08 mmol) in tetrahydrofuran (35 mL), cooled to - 78 °C, was added. The temperature of the reaction mixture was maintained at -30 °C for 2 hours, before being allowed to rise to room temperature at which temperature it was stirred for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (150 mL) and water (150 mL), the latter then being extracted with MTBE (3 x 150 mL). The combined organic extracts were dried over sodium sulfate and evaporated. The residue was purified by silica-gel column chromatography on a 330 g column, eluting from 0% to 15% of MTBE in heptane to provide 3 -trimethyl silylbut-3-en-l-ol (8.62 g, 68%) as a yellowish oil. NMR (400 MHz, CDCb) d 5.69 - 5.65 (m, 1H), 5.48 (d, J = 2.9 Hz, 1H), 3.69 (q, J = 6.4 Hz, 2H), 2.44 (t, J = 6.6 Hz, 2H), 1.44 (br. s., 1H), 0.15 - 0.08 (m, 9H). ESI-MS m/z calc. 144.097, found 145.2 (M+l)+; Retention time: 1.723 minutes (LC method E).
With copper(l) iodide; magnesium; ethylene dibromide 1.) tetrahydrofuran, 40 deg C, 1 h, 2.) tetrahydrofuran, -30 deg C, 5 h; R.T. overnight; Yield given. Multistep reaction;
With copper(l) iodide; magnesium 1.) THF; Yield given. Multistep reaction;

  • 4
  • [ 503-30-0 ]
  • [ 13683-41-5 ]
  • [ 112793-67-6 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; Stage #2: trimethylene oxide With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether at -78℃; for 0.25h;
77% With boron trifluoride diethyl etherate; sec.-butyllithium In tetrahydrofuran; diethyl ether; cyclohexane at -70℃; for 0.25h;
  • 5
  • [ 50-00-0 ]
  • [ 13683-41-5 ]
  • [ 55287-89-3 ]
YieldReaction ConditionsOperation in experiment
75% With tert.-butyl lithium In tetrahydrofuran; diethyl ether at -78℃;
66% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2.5h; Inert atmosphere; Stage #2: formaldehyd In diethyl ether at -78 - 20℃; for 2.5h; Inert atmosphere;
64% With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2.5h; Inert atmosphere;
With magnesium 1) THF, reflux, 1.5 h, 2) 10 h, room temperature; Yield given. Multistep reaction;
With tert.-butyl lithium Multistep reaction;
With [2,2]bipyridinyl; iodine; magnesium 1.) THF, reflux, 2.5 h, 2.) THF, from 50 deg C to 55 deg C, 5 h; Yield given. Multistep reaction;
With magnesium 1.) THF, 2.) -78 deg C; Multistep reaction;
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2.5h; Stage #2: formaldehyd In diethyl ether; pentane at -78 - 24℃; for 2.75h;
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 3h; Inert atmosphere; Stage #2: formaldehyd In diethyl ether; pentane at -78 - 20℃; Inert atmosphere;
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 3h; Inert atmosphere; Stage #2: formaldehyd In diethyl ether; pentane at -78 - 20℃; for 18h; Inert atmosphere;

  • 6
  • [ 463-49-0 ]
  • [ 13683-41-5 ]
  • [ 18424-76-5 ]
  • [ 119841-17-7 ]
YieldReaction ConditionsOperation in experiment
69% In dimethyl sulfoxide at 65℃; for 24h;
  • 7
  • [ 463-49-0 ]
  • [ 13683-41-5 ]
  • [ 1007476-32-5 ]
  • 2-Methoxymethyl-4-methylene-5-trimethylsilanyl-hex-5-enoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% In dimethyl sulfoxide at 65℃; for 24h;
  • 8
  • [ 1719-57-9 ]
  • [ 13683-41-5 ]
  • [ 96430-50-1 ]
YieldReaction ConditionsOperation in experiment
49% With tert.-butyl lithium In diethyl ether 1.) -78 deg C, 2 h; 2.) 1 h, -78 deg C;
  • 9
  • [ 13683-41-5 ]
  • [ 2684-60-8 ]
  • [ 86955-88-6 ]
YieldReaction ConditionsOperation in experiment
63% In diethyl ether at 0℃; for 4h;
  • 10
  • [ 13683-41-5 ]
  • [ 650-51-1 ]
  • [ 88180-99-8 ]
YieldReaction ConditionsOperation in experiment
48% In 1,2-dimethoxyethane; diethylene glycol dimethyl ether at 110℃;
In diethylene glycol dimethyl ether at 80 - 90℃; for 10h;
  • 11
  • [ 13683-41-5 ]
  • [ 113826-06-5 ]
  • Toluene-4-sulfonic acid (S)-2-hydroxy-4-trimethylsilanyl-pent-4-enyl ester [ No CAS ]
  • 12
  • [ 13683-41-5 ]
  • [ 1007-27-8 ]
  • [ 62762-20-3 ]
  • [ 7671-24-1 ]
YieldReaction ConditionsOperation in experiment
88% In benzene at 80℃; for 40h; Yields of byproduct given;
  • 13
  • [ 13683-41-5 ]
  • [ 111427-74-8 ]
  • 3-((2R,3S)-3-Benzyloxymethyl-oxiranyl)-2-trimethylsilanyl-undec-1-en-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.6% With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h;
  • 14
  • [ 13683-41-5 ]
  • [ 51666-94-5 ]
YieldReaction ConditionsOperation in experiment
With tert.-butyl lithium In tetrahydrofuran at -120℃;
With tert.-butyl lithium In diethyl ether; pentane at -78 - -15℃; for 2.5h;
  • 15
  • [ 13683-41-5 ]
  • [ 1066-54-2 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydroxide In dimethyl sulfoxide at 40 - 110℃; for 2h; 4; 5 [Example 4] Preparation of trimethylsilylacetylene Put 0.9mol sodium hydroxide and 100g dimethyl sulfoxide into a 500mL four-necked reaction flask, heat up to 40-110, add 0.8mol one-step product dropwise, drop the reaction for 2h, GC check the reaction is complete, filter, and distill the filtrate to obtain 134.6g of trimethylsilylacetylene, purity 99%, yield 94%.
  • 16
  • [ 13683-41-5 ]
  • [ 75-07-0 ]
  • [ 66374-47-8 ]
YieldReaction ConditionsOperation in experiment
57% With tert.-butyl lithium In pentane
With magnesium Multistep reaction;
With tert.-butyl lithium 1.) pentane, ether, -78 deg C, 2 h, 2.) pentane, ether, RT; Yield given. Multistep reaction;
  • 17
  • [ 13683-41-5 ]
  • [ 28663-68-5 ]
  • [ 86955-91-1 ]
YieldReaction ConditionsOperation in experiment
47% With triethylamine In diethyl ether at 25℃; for 48h;
  • 18
  • [ 13683-41-5 ]
  • [ 698-16-8 ]
  • [ 54773-27-2 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine In tetrachloromethane
60% With triethylamine In tetrachloromethane at 0℃; for 2h;
51% With triethylamine In diethyl ether for 4h;
  • 19
  • [ 13683-41-5 ]
  • [ 16033-71-9 ]
  • [ 82166-53-8 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium; methyl iodide In tetrahydrofuran for 1h; Reflux; Inert atmosphere; Stage #2: With copper(l) iodide In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #3: methyloxirane In tetrahydrofuran at 20℃; Inert atmosphere;
73% With tert.-butyl lithium In diethyl ether at -78 - 20℃;
Yield given. Multistep reaction;
  • 20
  • [ 754-05-2 ]
  • [ 13683-41-5 ]
YieldReaction ConditionsOperation in experiment
92.2% With bromine; triethylamine In dichloromethane at -10 - -5℃; Reflux; 2; 3 [Example 2] Preparation of 1-bromotrimethylsilyl ethylene Put 0.9 mol of trimethylsilyl ethylene, 2.25 mol of triethylamine and 400 ml of dichloromethane into a 1L four-necked reaction flask, control the temperature from -10 to -5°C, add 1.06 mol of liquid bromine dropwise, the addition is complete in 1 hour, reaction 2 -4h, reflux for 1-3h, GC detects that the trimethylsilylene reaction is complete. After cooling and filtering, the filtrate was distilled under reduced pressure to collect the distillate at 72-75°C to obtain 165g (92.2%) of 1-bromotrimethylsilyl ethylene.
81% With bromine; diethylamine at -78℃;
68% With bromine; diethylamine for 3h; Heating;
57% Stage #1: ethenyltrimethylsilane With bromine at -78 - 20℃; Stage #2: With diethylamine for 12h; Heating;
45% With bromine; diethylamine In water at -35 - 20℃; for 1.2h; Reflux; 1.1.2.1 Preparation of (1-bromovinyl)trimethylsilane Add vinyltrimethylsilane (100g) into a 2000ml three-necked bottle,Then the temperature is lowered to -35-30, and bromine water is slowly added dropwise, and heat is violently released during the dropwise addition.During the dripping process, keep the internal temperature between -30-10 (the internal temperature is lower than -30, the reaction system forms a solid), after the dripping is completed, naturally rise to room temperature, and slowly drip diethylamine (676ml),The initial dripping exothermics, after dripping, it is heated to reflux for 1.2h.After the completion of the reaction, the reaction solution was lowered to room temperature and diluted with ether (1000ml),Wash 2-3 times with water and then wash with 2N hydrochloric acid until the pH of the water layer is 1.The organic phase was washed with saturated sodium bicarbonate and saturated sodium chloride successively once,Add anhydrous sodium sulfate to dry, filter, and concentrate the filtrate. Vacuum distillation,Collect the fraction 80g (38-42°C). The yield was 45%.
With bromine; triethylamine Multistep reaction;
With bromine; diethylamine 1.) dichloromethane, -78 deg C, 10 min; R.T., 2.) no solvent, R.T., 7 d; Yield given. Multistep reaction;
With bromine; diethylamine 1.) -78 deg C; Multistep reaction;
Multi-step reaction with 2 steps 1: 91 percent / Br2 2: 82 percent / (C2H5)2NH / 168 h
Multi-step reaction with 2 steps 1: 39 percent / bromine / -78 °C 2: 59 percent / diethylamine
Stage #1: ethenyltrimethylsilane With bromine at -78℃; for 1h; Inert atmosphere; Stage #2: With diethylamine for 12h; Reflux;

  • 21
  • [ 75-77-4 ]
  • [ 593-60-2 ]
  • [ 13683-41-5 ]
  • [ 14630-40-1 ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 7 % Chromat. With lithium diisopropyl amide In tetrahydrofuran; diethyl ether at -100℃; for 3h;
Stage #1: Vinyl bromide With n-butyllithium; lithium bromide In tetrahydrofuran; diethyl ether; pentane at -110 - -108℃; for 0.75h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; diethyl ether; pentane at -105 - -100℃; for 1h;
  • 22
  • [ 40365-61-5 ]
  • [ 13683-41-5 ]
  • 5-Trimethylsilanyl-hex-5-en-3-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tetrakis(triphenylphosphine) palladium(0); N-butylamine In N,N-dimethyl-formamide Ambient temperature;
  • 23
  • [ 18669-04-0 ]
  • [ 13683-41-5 ]
  • 4-(trimethylsilyl)-4-penten-2-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); N-butylamine In N,N-dimethyl-formamide Ambient temperature;
  • 24
  • [ 13683-41-5 ]
  • 3β-<(Tetrahydro-2H-pyran-2'-yl)oxy>-5β-androst-15-en-17-one [ No CAS ]
  • [ 163431-29-6 ]
YieldReaction ConditionsOperation in experiment
91% With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran; hexane 1.) -25 deg C, 1 h, 2.) -25 deg C to r.t., 1 h;
  • 25
  • [ 13683-41-5 ]
  • [ 116103-20-9 ]
YieldReaction ConditionsOperation in experiment
84% With iodine; tert.-butyl lithium
95 %Chromat. With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium iodide In tetrahydrofuran at 70℃; for 15h; 34 Example [34;] [1-IODO-1-TRIMETHYYL) ETHYLENE] A Schlenk tube was charged with CuI (9.6 mg, 0.0504 mmol, 5.0 mol%), NaI (300 mg, 2.00 mmol), evacuated and backfilled with argon. trans-N,N'-Dimethyl-1, 2- cyclohexanediamine [(16 GEL,] 0.10 mmol, 10 mol%), [L-BROMO-L-(TRIMETHYLSILYL)] ethylene [(15555, IL,] 1.00 mmol), and THF (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [70 °C] for 15 h. The resulting suspension was allowed to reach room temperature. Dichloromethane (2 mL) and dodecane (internal GC standard, 230 µL) were added to the reaction mixture. A [50 ; JE] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide 95% conversion of 1-bromo-1-(trimethylsilyl) ethylene and clean formation of 1-iodo-1-(trimethylsilyl) ethylene.
  • 26
  • [ 13683-41-5 ]
  • [ 107-19-7 ]
  • 4-(trimethylsilyl)-4-penten-2-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); N-butylamine In N,N-dimethyl-formamide Ambient temperature;
27% With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) Inert atmosphere; Darkness;
  • 27
  • [ 74213-24-4 ]
  • [ 13683-41-5 ]
  • 3-Bromo-5-trimethylsilanyl-isoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate In ethyl acetate
  • 28
  • [ 4282-40-0 ]
  • [ 13683-41-5 ]
  • [ 119547-50-1 ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 1-Iodoheptane In tetrahydrofuran at -78 - 20℃;
  • 29
  • [ 13683-41-5 ]
  • [ 51849-22-0 ]
  • [ 243656-65-7 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In tetrahydrofuran for 0.5h; Heating; Stage #2: iodomethyl phenyl sulfide In tetrahydrofuran at 0℃; for 1h;
  • 30
  • [ 13683-41-5 ]
  • [ 15186-48-8 ]
  • [ 102357-25-5 ]
YieldReaction ConditionsOperation in experiment
76% With copper(l) iodide; magnesium In tetrahydrofuran
  • 31
  • [ 13683-41-5 ]
  • [ 145483-68-7 ]
  • [ 347307-94-2 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 1,4-diiodo-2,5-dioctyloxybenzene With magnesium In tetrahydrofuran for 1h; Heating; Stage #2: 1-bromo-1-(trimethylsilyl)ethene In tetrahydrofuran at 0 - 20℃; Further stages.;
  • 32
  • [ 29325-28-8 ]
  • [ 13683-41-5 ]
  • (1R,2R,6S,7S)-4,4-Dimethyl-3,5,12-trioxa-tricyclo[5.4.1.02,6]dodec-8-ene [ No CAS ]
  • (1R,2R,6S,7S)-4,4-Dimethyl-3,5,12-trioxa-tricyclo[5.4.1.02,6]dodec-9-ene [ No CAS ]
  • ((1R,2R,6S,7S)-4,4-Dimethyl-3,5,12-trioxa-tricyclo[5.4.1.02,6]dodec-9-en-9-yl)-trimethyl-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 33% 2: 5% 3: 19% Stage #1: (3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-6-vinyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran Stage #2: 1-bromo-1-(trimethylsilyl)ethene With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) In benzene Heating; Stage #3: With tin(IV) chloride In dichloromethane at -78 - -10℃; for 5h; Further stages.;
  • 33
  • [ 13683-41-5 ]
  • [ 432502-68-6 ]
  • [ 432502-74-4 ]
YieldReaction ConditionsOperation in experiment
33% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium In tetrahydrofuran Stage #2: dimethyl(oxiranyloxy)phenylsilane With boron trifluoride diethyl etherate In tetrahydrofuran at -60 - 20℃; for 12h;
  • 34
  • [ 104-53-0 ]
  • [ 13683-41-5 ]
  • [ 88257-48-1 ]
YieldReaction ConditionsOperation in experiment
74% With tert.-butyl lithium In diethyl ether at -78 - 20℃;
  • 35
  • [ 13683-41-5 ]
  • [ 86953-79-9 ]
  • N-[(1,1-dimethylethoxy)carbonyl]-2-[1-(trimethylsilyl)ethenyl]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: tert-butyl pyrrolidine-1-carboxylate With sec.-butyllithium; (-)-sparteine In tetrahydrofuran at -78℃; for 1h; Stage #2: With lithium chloride In tetrahydrofuran at -78℃; for 1h; Stage #3: 1-bromo-1-(trimethylsilyl)ethene In tetrahydrofuran at -78 - 25℃; for 12h;
  • 36
  • [ 13683-41-5 ]
  • [ 829-85-6 ]
  • [ 125708-42-1 ]
YieldReaction ConditionsOperation in experiment
93% With triethylamine In N,N-dimethyl-formamide at 120℃; for 0.5h;
  • 37
  • [ 13683-41-5 ]
  • [ 42331-17-9 ]
  • (Z)-1-phenyl-2-(3-trimethylsilylallyl)pyrrolidine [ No CAS ]
  • (E)-1-phenyl-2-(3-trimethylsilylallyl)pyrrolidine [ No CAS ]
  • 1-phenyl-2-(2-trimethylsilylallyl)pyrrolidine [ No CAS ]
  • (2R,3S)-2-Methyl-1-phenyl-3-(1-trimethylsilanyl-vinyl)-pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifuran-2-yl-phosphane; sodium t-butanolate In toluene at 110℃; Title compound not separated from byproducts;
  • 38
  • [ 13683-41-5 ]
  • [ 122775-35-3 ]
  • [ 120093-94-9 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate In ethanol; benzene at 80℃; for 20h;
  • 39
  • [ 486-25-9 ]
  • [ 13683-41-5 ]
  • [ 386253-16-3 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In tetrahydrofuran Stage #2: 9-fluorenone In tetrahydrofuran for 2h; Further stages.;
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In diethyl ether Stage #2: 9-fluorenone
  • 40
  • [ 13683-41-5 ]
  • [ 40138-16-7 ]
  • [ 120093-90-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; toluene at 80℃;
  • 41
  • 3-Bromo-but-1-yne [ No CAS ]
  • [ 13683-41-5 ]
  • (1E,5E)-3,4-Bis-eth-(E)-ylidene-1,6-bis-trimethylsilanyl-cycloocta-1,5-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With indium; tetrakis(triphenylphosphine) palladium(0); lithium chloride In tetrahydrofuran at 50℃; for 2h;
  • 42
  • [ 886976-22-3 ]
  • [ 13683-41-5 ]
  • [ 886976-30-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 2.5h; Stage #2: 4-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-hex-4-enal In diethyl ether; pentane at -78 - 0℃; for 0.5h;
  • 43
  • [ 13683-41-5 ]
  • [ 106-96-7 ]
  • 3,4-dimethylene-1,6-bis-trimethylsialnyl-cycloocta-1,5-diene [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With indium; tetrakis(triphenylphosphine) palladium(0); lithium chloride In tetrahydrofuran at 50℃; for 2h;
71% Stage #1: propargyl bromide With indium In N,N-dimethyl-formamide; toluene Stage #2: 1-bromo-1-(trimethylsilyl)ethene With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide; toluene at 50℃; for 2h;
  • 44
  • Triisopropyl-[(2R,3R)-2-methoxy-3-((2R,3R)-3-methyl-oxiranyl)-butoxy]-silane [ No CAS ]
  • [ 13683-41-5 ]
  • (+/-)-(2R,3S,4S,5R)-4-hydroxy-3,5-dimethyl-6trimethylsilyl-2-methoxy-1-[(triisopropylsilyl)oxy]-6-heptene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With iodine; magnesium In tetrahydrofuran for 1h; Heating; Stage #2: With copper(l) iodide In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; Stage #3: Triisopropyl-[(2R,3R)-2-methoxy-3-((2R,3R)-3-methyl-oxiranyl)-butoxy]-silane In tetrahydrofuran; diethyl ether at -78 - 20℃;
  • 45
  • [ 13683-41-5 ]
  • 3-trimethylsilanylindan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pd(PPh3)4; aq. Na2CO3 / toluene; methanol / 80 °C 2: [Rh(R-BINAP)(NBD)]ClO4; H2 / CH2Cl2 / 120 h / 20 °C
  • 46
  • [ 13683-41-5 ]
  • 3-trimethylsilanylindan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pd(PPh3)4; aq. Na2CO3 / toluene; methanol / 80 °C 2: [Rh(R-BINAP)(NBD)]ClO4; H2 / CH2Cl2 / 120 h / 20 °C
  • 47
  • [ 13683-41-5 ]
  • 3-(trimethylsilyl)indan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Pd(PPh3)4; aq. Na2CO3 / toluene; methanol / 80 °C 2: 93 percent / [Rh(dppe)(NBD)]ClO4; H2 / CH2Cl2 / 2 h / 23 °C
  • 48
  • [ 13683-41-5 ]
  • [ 112793-68-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: t-BuLi / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 1.2: 91 percent / BF3*Et2O / diethyl ether; tetrahydrofuran / 0.25 h / -78 °C 2.1: 84 percent / pyridine-sulfur trioxide complex; triethylamine / CH2Cl2; dimethylsulfoxide / 1.5 h / 20 °C
Multi-step reaction with 2 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h
  • 49
  • [ 13683-41-5 ]
  • [ 112793-70-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C
  • 50
  • [ 13683-41-5 ]
  • [ 112793-72-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 21 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C
  • 51
  • [ 13683-41-5 ]
  • [ 112817-44-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C
  • 52
  • [ 13683-41-5 ]
  • [ 112793-91-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide 8: 60 percent / diisopropylethylamine / CH2Cl2 / 4 h / 23 °C 9: 24 percent / SnCl4 / CH2Cl2 / 2 h / -15 °C
  • 53
  • [ 13683-41-5 ]
  • [ 112793-94-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 96 percent / PPTs / benzene / Heating
  • 54
  • [ 13683-41-5 ]
  • [ 112793-95-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide 8: 90 percent / PPTs / CH2Cl2 9: 30 percent / SnCl4 / CH2Cl2 / 2 h / -20 °C
Multi-step reaction with 8 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 96 percent / PPTs / benzene / Heating 8: 24 percent / SnCl4 / 15 h / 23 °C
  • 55
  • [ 13683-41-5 ]
  • [ 112793-90-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide
  • 56
  • [ 13683-41-5 ]
  • {(S)-4-Chloro-1-methylene-4-[(S)-((E)-2-propenyl)-[1,3]dioxolan-4-yl]-butyl}-trimethyl-silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 92 percent / PPTs / benzene / Heating
  • 57
  • [ 13683-41-5 ]
  • [ 112794-03-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide
  • 58
  • [ 13683-41-5 ]
  • (5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-6-(1-ethoxy-butoxy)-2-trimethylsilanyl-hept-1-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide 8: 90 percent / PPTs / CH2Cl2
  • 59
  • [ 13683-41-5 ]
  • [ 112794-02-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide 8: acid
  • 60
  • [ 13683-41-5 ]
  • (5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-chloro-6-((E)-1-ethoxy-but-2-enyloxy)-2-trimethylsilanyl-hept-1-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide 8: 38 percent / 1,2,2,6,6-pentamethylpiperidine / CH2Cl2 9: 85 percent / DBU / toluene / 120 °C
  • 61
  • [ 13683-41-5 ]
  • Acetic acid 1-[(1S,2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-chloro-5-trimethylsilanyl-hex-5-enyloxy]-ethoxy-methyl}-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 77 percent / sec-BuLi, BF3*OEt2 / tetrahydrofuran; cyclohexane; diethyl ether / 0.25 h / -70 °C 2: 89 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 2 h 3: 18-crown-6, KN(TMS)2 / tetrahydrofuran; toluene / 0.5 h / -70 °C 4: 93 percent / diisobutylaluminium hydride / hexane; CH2Cl2 / 1 h / -70 to -20 deg C 5: 78 percent / molecular sieves (4 Angstroem), (+)-diethyl L-tartrate, titanium tetraisopropoxide, tert-butyl hydroperoxide / CH2Cl2; 2,2,4-trimethyl-pentane / 15 h / 4 °C 6: 68 percent / trimethylamine hydrochloride, titanium tetraisopropoxide / CH2Cl2 / 15 h / 23 °C 7: 93 percent / imidazole / dimethylformamide 8: acid
  • 62
  • [ 13683-41-5 ]
  • [ 5396-91-8 ]
  • [ 919285-09-9 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In diethyl ether; pentane at -78℃; Stage #2: 1,5-diphenyl-3-pentanone In diethyl ether; pentane at 0℃; Stage #3: In diethyl ether; N,N-dimethyl-formamide; pentane at 80℃; Further stages.;
  • 63
  • [ 18922-04-8 ]
  • [ 13683-41-5 ]
  • C11H22Si [ No CAS ]
  • [ 22472-36-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-1-(trimethylsilyl)ethene Stage #2: 6-iodohex-1-ene With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h; Further stages. Title compound not separated from byproducts.;
  • 64
  • [ 13683-41-5 ]
  • [ 14660-52-7 ]
  • [ 954412-44-3 ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: 1-bromo-1-(trimethylsilyl)ethene Stage #2: ethyl 5-bromovalerate With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h; Further stages.;
  • 65
  • [ 13683-41-5 ]
  • [ 1200-03-9 ]
  • [ 954412-43-2 ]
  • [ 2653-89-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-1-(trimethylsilyl)ethene Stage #2: 4-bromophenyl butyl ether With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h; Further stages. Title compound not separated from byproducts.;
  • 66
  • [ 13683-41-5 ]
  • [ 954412-31-8 ]
  • [ 954412-46-5 ]
  • [ 954412-41-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-1-(trimethylsilyl)ethene Stage #2: C20H27IOSi With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h; Further stages. Title compound not separated from byproducts.;
  • 67
  • [ 13683-41-5 ]
  • [ 143-15-7 ]
  • [ 954412-42-1 ]
  • [ 112-41-4 ]
  • [ 22472-36-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-1-(trimethylsilyl)ethene Stage #2: 1-dodecylbromide With N,N,N,N,-tetramethylethylenediamine; iron(III) chloride In tetrahydrofuran at 0℃; for 0.5h; Further stages. Title compound not separated from byproducts.;
  • 68
  • [ 13683-41-5 ]
  • [ 1066-45-1 ]
  • [ 87241-31-4 ]
YieldReaction ConditionsOperation in experiment
76% With magnesium In tetrahydrofuran under Ar, soln. of Br-compd. added slowly to Mg in THF with refluxing, refluxed for 1 h, cooled to room temp., soln. of Me3SnCl added within 1 h, stirred for several h; ether and saturated NH4Cl-soln. added, organic layer dried over MgSO4, fractionated at the water pump, elem. anal.;
  • 69
  • [ 13683-41-5 ]
  • [ 333-27-7 ]
  • [ 199620-15-0 ]
  • [((1-(trimethylsilyl)ethenyl)methoxymethylene)pentacarbonylmolybdenum(0)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With sec.-butyllithium In tetrahydrofuran; diethyl ether; cyclohexane s-BuLi is added to a soln. of the silane in THF at -78°C, after 30. min warmed to 0°C, added to a slurry of Mo(CO)6 in diethyl ether, after 1 h CF3SO3CH3 is added, stirred for 15 min, warmed to room temp.; NaHCO3 soln. and NaCl soln. are added, the organic phase is dried, concd., chromd.;
  • 70
  • [ 629-05-0 ]
  • [ 13683-41-5 ]
  • [ 1089192-07-3 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: n-octyne With methylmagnesium bromide In tetrahydrofuran at 0 - 60℃; for 4h; Inert atmosphere; Stage #2: With iron(III) chloride; lithium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: 1-bromo-1-(trimethylsilyl)ethene In tetrahydrofuran at 0 - 60℃; for 12h; Inert atmosphere;
89% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine at 70℃; for 12h; Inert atmosphere; Schlenk technique;
  • 71
  • [ 13683-41-5 ]
  • [ 86318-61-8 ]
  • [ 1089192-11-9 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: (tert-butyldimethylsilyl)acetylene With methylmagnesium bromide In tetrahydrofuran at 0 - 60℃; for 4h; Inert atmosphere; Stage #2: With iron(III) chloride; lithium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: 1-bromo-1-(trimethylsilyl)ethene In tetrahydrofuran at 0 - 60℃; for 24h; Inert atmosphere;
  • 72
  • [ 13683-41-5 ]
  • [ 89343-06-6 ]
  • [ 1089192-12-0 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: tris-iso-propylsilyl acetylene With methylmagnesium bromide In tetrahydrofuran at 0 - 60℃; for 4h; Inert atmosphere; Stage #2: With iron(III) chloride; lithium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: 1-bromo-1-(trimethylsilyl)ethene In tetrahydrofuran at 0 - 60℃; for 24h; Inert atmosphere;
  • 73
  • [ 13683-41-5 ]
  • [ 91266-03-4 ]
  • [ 1089192-10-8 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: tert-butyl-pent-4-ynyloxy-diphenyl-silane With methylmagnesium bromide In tetrahydrofuran at 0 - 60℃; for 4h; Inert atmosphere; Stage #2: With iron(III) chloride; lithium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: 1-bromo-1-(trimethylsilyl)ethene In tetrahydrofuran at 0 - 60℃; for 24h; Inert atmosphere;
  • 74
  • [ 13683-41-5 ]
  • [ 536-74-3 ]
  • trimethyl(4-phenylbut-1-en-3-yn-2-yl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: phenylacetylene With methylmagnesium bromide In tetrahydrofuran at 0 - 60℃; for 4h; Inert atmosphere; Stage #2: With iron(III) chloride; lithium bromide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #3: 1-bromo-1-(trimethylsilyl)ethene In tetrahydrofuran at 0 - 60℃; for 24h; Inert atmosphere;
  • 75
  • [ 13683-41-5 ]
  • tert-butyldimethylsilyl (S)-glycidyl ether [ No CAS ]
  • [ 950764-90-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In tetrahydrofuran at 60℃; for 0.75h; Inert atmosphere; Reflux; Stage #2: tert-butyldimethylsilyl (S)-glycidyl ether With copper(l) cyanide In tetrahydrofuran at -30 - 20℃; for 2.08333h; Inert atmosphere;
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; Stage #2: With copper(l) iodide In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere; Stage #3: tert-butyldimethylsilyl (S)-glycidyl ether In tetrahydrofuran at -40 - 20℃;
  • 76
  • [ 13683-41-5 ]
  • [ 124150-87-4 ]
  • [ 1162676-14-3 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In tetrahydrofuran at 60℃; for 0.75h; Inert atmosphere; Reflux; Stage #2: tert-butyldimethylsilyl (R)-glycidyl ether With copper(l) cyanide In tetrahydrofuran at -30 - 20℃; for 2.08333h; Inert atmosphere;
  • 77
  • [ 13683-41-5 ]
  • [ 119649-27-3 ]
  • [ 1219361-20-2 ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With tert.-butyl lithium In diethyl ether; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: 4-((4-methoxybenzyl)oxy)butanal In diethyl ether; pentane at -78℃; Inert atmosphere;
  • 78
  • [ 13683-41-5 ]
  • [ 1361412-47-6 ]
  • [ 1442111-87-6 ]
YieldReaction ConditionsOperation in experiment
95% With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;
  • 79
  • (2S,3S)-4-(tert-butyldiphenylsilanyloxy)-2,3-epoxy-1-iodobutane [ No CAS ]
  • [ 13683-41-5 ]
  • (4S,5S)-6-(tert-butyldiphenylsilanyloxy)-4,5-epoxy-2-trimethylsilylhex-1-ene [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium; ethylene dibromide In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux; Stage #2: (2S,3S)-4-(tert-butyldiphenylsilanyloxy)-2,3-epoxy-1-iodobutane With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide In tetrahydrofuran at -25℃; for 1h; Inert atmosphere;
  • 80
  • [ 13683-41-5 ]
  • [ 106-95-6 ]
  • [ 49763-80-6 ]
  • C10H18OSSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 1-bromo-1-(trimethylsilyl)ethene; carboethoxymethyl trimethylsilyl sulfide With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: allyl bromide In diethyl ether; pentane at -78 - 20℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; water In diethyl ether for 0.5h; Inert atmosphere; chemoselective reaction;
  • 81
  • [ 13683-41-5 ]
  • (2-((S)-oxiran-2-yl)ethoxy)(tert-butyl)dimethylsilane [ No CAS ]
  • C15H34O2Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In tetrahydrofuran; ethylene dibromide at 60℃; for 0.833333h; Inert atmosphere; Stage #2: (2-((S)-oxiran-2-yl)ethoxy)(tert-butyl)dimethylsilane With copper(l) cyanide In tetrahydrofuran; ethylene dibromide at -30 - 25℃; for 2h; Inert atmosphere;
  • 82
  • [ 13683-41-5 ]
  • [ 91111-12-5 ]
  • C16H26O4SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium In tetrahydrofuran; ethylene dibromide at 25 - 60℃; for 0.5h; Inert atmosphere; Stage #2: With copper(l) iodide In tetrahydrofuran; ethylene dibromide at -75℃; for 0.5h; Inert atmosphere; Stage #3: 2-(oxiran-2-yl)ethyl 4-methylphenylsulfonate In tetrahydrofuran; ethylene dibromide at -75 - -40℃; for 2h; Inert atmosphere;
  • 83
  • [ 13683-41-5 ]
  • C15H23NO2Si [ No CAS ]
  • C20H33NO2Si2 [ No CAS ]
  • C20H33NO2Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 67% 2: 7% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: C15H23NO2Si In tetrahydrofuran Inert atmosphere;
  • 84
  • [ 13683-41-5 ]
  • [ 286-20-4 ]
  • [ 67964-32-3 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium; methyl iodide In tetrahydrofuran for 1h; Reflux; Inert atmosphere; Stage #2: With copper(l) iodide In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #3: cyclohexane-1,2-epoxide In tetrahydrofuran at 20℃; Inert atmosphere;
Same Skeleton Products
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