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CAS No. : | 7237-34-5 | MDL No. : | MFCD00011901 |
Formula : | C20H20BrOP | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QZJOQNHOOVSESC-UHFFFAOYSA-M |
M.W : | 387.25 | Pubchem ID : | 2733550 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
In toluene; for 24h;Reflux; | General procedure: A typical procedure for the preparation of [Ph3PC2H4NH2]Br (1c) is as follows: A solution of triphenylphosphine (5 mmol) and 2-bromoethylamine hydrobromide (5 mmol) in 20 mL toluene was heated and subject to reflux for 24 h. After cooling, the resulted crude solid was filtered out, and stirred in 10 mL triethylamine for 4 h. Afterward, the triethylamine was removed, and the as obtained solid was washed three times with ethyl acetate, then dried at 60 C under vacuum for 12 h to give product 1c in the form of a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane; water; | i) To a stirred suspension of 2-hydroxyethyltriphenylphosphonium bromide (30 g, 0.077 mol) in dried tetrahydrofuran (300 ml) cooled to -40 C. under an atmosphere of nitrogen was added a solution of n-butyllithium in hexane (2.5M, 58.5 ml) dropwise. The resulting orange suspension was then stirred at 50 C. with occasional ultrasonication for 3 h, cooled to -60 C. and a solution of 3-(4-ethoxyphenyl)-2-methylpropenaldehyde (7.4 g, 0.039 ml) in dried tetrahydrofuran (25 ml) added dropwise and allowed to warm to 0 C. After 1/2 h, water was added and the organic phase separated. The aqueous phase was extracted with diethyl ether and the combined organic phases washed four times with water and then brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to an oil. The oil was dissolved in a minimum of diethyl ether and chromatographed on flash silica eluding with hexane then hexane-diethyl ether (3:2) to give 5-(4-ethoxyphenyl)-4-methylpent-2E,4E-dienal as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Lithium bis(trimethylsilyl)amide (18.4 mL, 18.4 mmol, 1.0 M in THF) is added dropwise to a suspension of (2-hydroxyethyl)triphenylphosphonium bromide (3.37 g, 8.70 mmol) in 60 mL of THF at 0 C. After 1 hour, the golden brown solution is treated with a solution of the compound from f) (1.4 g, 3.48 mmol) in 10 mL of THF dropwise. The resulting reaction mixture is stirred at 0 C. for 40 minutes and then quenched with saturated aqueous NH4Cl. The resulting mixture is extracted with EtOAc (2×), and the combined organic extracts are dried (Na2SO4), filtered, and evaporated to give a brown oil. Purification by silica gel column chromatography (gradient from 20% EtOAc/Hex to 75% EtOAc/Hex) affords the title compound as a yellow, viscous oil (680 mg, 45%). | |
45% | g) 4-((6R,8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-yl)but-2-en-1-ol - Lithium bis(trimethylsilyl)amide (18.4 mL, 18.4 mmol, 1.0 M in THF)is added dropwise to a suspension of (2-hydroxyethyl) triphenylphosphonium bromide (3.37 g, 8.70 mmol) in 60 mL ofTHF at 0C. After 1 hour, the golden brown solution is treated with a solution of the compound from f) (1.4 g, 3.48 mmol)in 10 mL of THF dropwise. The resulting reaction mixture is stirred at 0C for 40 minutes and then quenched with saturated aqueous NH4Cl. The resulting mixture is extracted with EtOAc (2x), and the combined organic extracts are dried (Na2SO4),filtered, and evaporated to give a brown oil. Purification by silica gel column chromatography (gradient from 20%EtOAc/Hex to 75% EtOAc/Hex) affords the title compound as a yellow, viscous oil (680 mg, 45%). | |
45% | Lithium bis(trimethylsilyl)amide (18.4 mL, 18.4 mmol, 1.0 M in THF) is added dropwise to a suspension of (2-hydroxyethyl) triphenylphosphonium bromide (3.37 g, 8.70 mmol) in 60 mL of THF at 0C. After 1 hour, the golden brown solution is treated with a solution of the compound from f) (1.4 g, 3.48 mmol) in 10 mL of THF dropwise. The resulting reaction mixture is stirred at 0C. for 40 minutes and then quenched with saturated aqueous NH4Cl. The resulting mixture is extracted with EtOAc (2), and the combined organic extracts are dried (Na2SO4), filtered, and evaporated to give a brown oil. Purification by silica gel column chromatography (gradient from 20% EtOAc/Hex to 75% EtOAc/Hex) affords the title compound as a yellow, viscous oil (680 mg, 45%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | Lithium bis(trimethylsilyl)amide (4.3 mL, 4.29 mmol, 1.0 M in THF) is added dropwise to a suspension of (2-hydroxyethyl)triphenylphosphonium bromide (786 mg, 2.03 mmol) in 14 mL of THF at 0 C. After 30 minutes, the golden brown solution is treated with a solution of the compound from h) (345 mg, 0.81 mmol) in 2 mL of THF dropwise. The resulting reaction mixture is stirred at 0 C. for 20 minutes and quenched with saturated aqueous NH4Cl. The resulting mixture is extracted with EtOAc (2×), and the combined organic extracts are dried (Na2SO4), filtered, and evaporated to give a brown oil. Purification by silica gel column chromatography (gradient from 5% EtOAc/CH2Cl2 to 40% EtOAc/CH2Cl2) affords the title compound as a yellow, viscous oil (140 mg, 38%). | |
38% | i) 6-((6R,8R,9S,13S,14S,17S)-3,17-bis(methoxymethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-yl)hexa-2,4-dien-1-ol- Lithium bis(trimethylsilyl)amide (4.3 mL, 4.29 mmol, 1.0 M inTHF) is added dropwise to a suspension of (2-hydroxyethyl) triphenylphosphonium bromide (786 mg, 2.03 mmol) in 14mL of THF at 0C. After 30 minutes, the golden brown solution is treated with a solution of the compound from h) (345mg, 0.81 mmol) in 2 mL of THF dropwise. The resulting reaction mixture is stirred at 0C for 20 minutes and quenchedwith saturated aqueous NH4Cl. The resulting mixture is extracted with EtOAc (2x), and the combined organic extractsare dried (Na2SO4), filtered, and evaporated to give a brown oil. Purification by silica gel column chromatography (gradientfrom 5% EtOAc/CH2Cl2 to 40% EtOAc/CH2Cl2) affords the title compound as a yellow, viscous oil (140 mg, 38%). | |
38% | Lithium bis(trimethylsilyl)amide (4.3 mL, 4.29 mmol, 1.0 M in THF) is added dropwise to a suspension of (2-hydroxyethyl) triphenylphosphonium bromide (786 mg, 2.03 mmol) in 14 mL of THF at 0C. After 30 minutes, the golden brown solution is treated with a solution of the compound from h) (345 mg, 0.81 mmol) in 2 mL of THF dropwise. The resulting reaction mixture is stirred at 0C. for 20 minutes and quenched with saturated aqueous NH4Cl. The resulting mixture is extracted with EtOAc (2), and the combined organic extracts are dried (Na2SO4), filtered, and evaporated to give a brown oil. Purification by silica gel column chromatography (gradient from 5% EtOAc/Ch2Cl2 to 40% EtOAc/CH2Cl2) affords the title compound as a yellow, viscous oil (140 mg, 38%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.49 g | With sodium hydroxide; In tetrahydrofuran; water; at 60℃; for 4h; | Synthesis of 3-(2,4,6-trimethoxy-phenyl)-but-2-en-1-ol [0073] 4.00 g of 2,4,6-trimethoxyacetophenone and 8.10 g of (2-hydroxyethyl)triphenyphosphonium bromide are added to 40 g of tetrahydrofuran. 3.80 g of 40% aqueous sodium hydroxide is added to the tetrahydrofuran mixture containing 2,4,6-trimethoxyaetophenone and (2-hydroxyethyl)triphenyphosphonium bromide. The mixture is stirred at 60 degrees Celsius for 4 hours and the mixture is filtrated. Afterwards, the tetrahydrofuran is distilled away and 40 g of cyclohexane is added to the residue. The cyclohexane mixture is stirred for 10 minutes and a deposit is filtrated and the filtrate is collected. Thereafter, cyclohexane is distilled away, and the resultant is purified by silica gel column chromatography (ethyl acetate: hexane=10:90). Thereby 3.49 g of 3-(2,4,6-trimethoxy-phenyl)-but-2-en-1-ol is obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The 319g brominated (2-hydroxy ethyl) phosphite added to the electrically conductive coating when in 2L2-methyl tetrahydrofuran, temperature control 0-30C, adding 124g tert potassium butanolate, stirring 40 min after, adding 174g between trifluoromethyl benzaldehyde, heating to 50-60C, stir until the reaction is complete, cooling to 20-30 C rear, add 2L the 1N hydrochloric acid after evenly stirring, static hierarchical, heating the upper layer of the organic layer to obtain 3 - (3-trifluoromethyl phenyl) 2-propen -1 alcohol 2-methyl tetrahydrofuran solution |
Tags: 7237-34-5 synthesis path| 7237-34-5 SDS| 7237-34-5 COA| 7237-34-5 purity| 7237-34-5 application| 7237-34-5 NMR| 7237-34-5 COA| 7237-34-5 structure
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