There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
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 : |
|
Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P210 | UN#: | 1993 |
Hazard Statements: | H225 | Packing Group: | Ⅱ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With diethylamine for 168h; | |
59% | With diethylamine | |
With diethylamine |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In dimethyl sulfoxide at 65℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | In dimethyl sulfoxide at 65℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With tert.-butyl lithium In diethyl ether 1.) -78 deg C, 2 h; 2.) 1 h, -78 deg C; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In diethyl ether at 0℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In 1,2-dimethoxyethane; diethylene glycol dimethyl ether at 110℃; | |
In diethylene glycol dimethyl ether at 80 - 90℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In benzene at 80℃; for 40h; Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.6% | With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tert.-butyl lithium In tetrahydrofuran at -120℃; | ||
With tert.-butyl lithium In diethyl ether; pentane at -78 - -15℃; for 2.5h; |
Yield | Reaction Conditions | Operation 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%. |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With triethylamine In diethyl ether at 25℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With triethylamine In tetrachloromethane | |
60% | With triethylamine In tetrachloromethane at 0℃; for 2h; | |
51% | With triethylamine In diethyl ether for 4h; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With tetrakis(triphenylphosphine) palladium(0); N-butylamine In N,N-dimethyl-formamide Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With tetrakis(triphenylphosphine) palladium(0); N-butylamine In N,N-dimethyl-formamide Ambient temperature; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium carbonate In ethyl acetate |
Yield | Reaction Conditions | Operation 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℃; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(l) iodide; magnesium In tetrahydrofuran |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With tert.-butyl lithium In diethyl ether at -78 - 20℃; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine In N,N-dimethyl-formamide at 120℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifuran-2-yl-phosphane; sodium t-butanolate In toluene at 110℃; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With sodium carbonate In ethanol; benzene at 80℃; for 20h; |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With indium; tetrakis(triphenylphosphine) palladium(0); lithium chloride In tetrahydrofuran at 50℃; for 2h; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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℃; |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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 |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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.; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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℃; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |
Yield | Reaction Conditions | Operation 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; |