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CAS No. : | 19493-09-5 | MDL No. : | N/A |
Formula : | C19H17P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 276.31 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Class: | N/A | |
Precautionary Statements: | UN#: | N/A | |
Hazard Statements: | Packing Group: | N/A |
* 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 diethyl ether Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In dimethyl sulfoxide; benzene at 25℃; for 2h; | |
80% | In tetrahydrofuran at -20 - 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In tetrahydrofuran 1.) 50-60 deg C, 2.) RT, overnight; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In benzene at 120 - 130℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 76% 2: 58% | In tetrahydrofuran at -30℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 76% 2: 58% | In tetrahydrofuran at -30℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran 1.) -78 deg C, 1 h, 2.) room temp., 0.5 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.6% | In benzene at 50℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In tetrahydrofuran; benzene for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In diethyl ether at 0℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In diethyl ether at 0 - 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisobutylaluminium hydride 1) PhCH3, -78 deg C, 2) PhCH3; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dimethyl sulfoxide at 65℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In tetrahydrofuran for 0.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 23% | In tetrahydrofuran for 0.75h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In dimethyl sulfoxide for 0.5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In tetrahydrofuran at -78℃; for 12h; to RT; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In tetrahydrofuran at -78 - 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.0 g | In diethyl ether at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; hexanes; at -30 - 20℃; for 16.1667h; | Procedure II INTERMEDIATE II.1: 1-Fluoro-2-methoxy-4-vinylbenzene To a stirred suspension of methyltriphenylphosphonium bromide (68.20 g, 0.191 mol) in anhydrous THF (400 mL) cooled to -40 C. was added n-butyllithium (2.5 M in hexanes, 71.2 mL, 0.178 mol) via syringe over 15 min, at which point the characteristic yellow color of the phosphorus ylide persisted. The reaction mixture was warmed to -10 C. over 1 h to complete the reaction. The mixture was subsequently cooled to -30 C. and a solution of 4-fluoro-3-methoxybenzaldehyde (10.00 g, 63.64 mmol) in anhydrous THF (40 mL) was added via a cannula over 10 min. The resultant mixture was warmed to ambient temperature over 16 h. The reaction was quenched by gradual addition of water (200 mL) and the aqueous extracted with diethyl ether (3×200 mL). The combined organic layers were washed with water (2×200 mL), brine (200 mL), dried (MgSO4) and concentrated under reduced pressure to give 1-fluoro-2-methoxy-4-vinylbenzene (INTERMEDIATE II.1) (8.69 g, 57.1 mmol, 90 %) as a yellow oil. Data for 1-fluoro-2-methoxy-4-vinylbenzene (INTERMEDIATE II.1): 1H NMR (300 MHz, CDCl3): delta 7.05-6.90 (m, 3H), 6.67 (dd, 1H), 5.67 (d, 1H), 5.24 (d, 1H), 3.92 9s, 3H) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50.6 percent / benzene / 3 h / 50 °C 2: benzene / 4 h / Heating | ||
Multi-step reaction with 2 steps 1: 50.6 percent / benzene / 3 h / 50 °C 2: Ph2AsCl / benzene / 4 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: diethyl ether 2: HCl / diethyl ether 3: aq. NaOH / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With NaH; In tetrahydrofuran; mineral oil; | Example 20 Synthesis of Tert.Thiols Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester were prepared from BOC-Hyp-OH following literature procedure [Baldwin, Jack E.; Field, Robert A.; Lawrence, Christopher C.; Merritt, Kristen D.; Schofield, Christopher J.; Tetrahedron Lett.; 34; 1993; 7489-7492; and Herdewijn, Piet; Claes, Paul J.; Vanderhaeghe, Hubert; Can.J.Chem.; 60; 1982; 2903-2907;] To a solution of methylenetriphenyl phosphorane, previously prepared from 37 g (777 mmol, 50% NaH in mineral oil, 4 eq) and 277.6 g (777 mmol, 4 eq) methyltriphenyl-phosphonium bromide in 1.5 1 THF by stirring at 50 C. for 4 h, were added 44.5 g (194 mmol, 1 eq) <strong>[84348-37-8](2S)-4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester</strong> in 300 ml over a period of 30 min at RT. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; toluene; at 0 - 20℃; for 18h; | Step A:To a stirred solution of methyltriphenylphosphonium bromide (9.1g, 12.8 mmol) in THF(50 ml) at 0C was added potassium hexamethyldisilazide (0.5M in tolue'ne, 48.6 ml), dropwise over 5min. The resulting mixture was allowed to warm up to room temperature over 1 h, then cooled again to0C and treated with methyl 4-formylbicyclo[2.2.2]octane-l-carboxylate (4-1) (Chapman, N. B. et al. J.Org. Chem., 1970, 35, 917) (2.5 g, 12.8 mmol). The reaction mixture was stirred at room temperature for18 h then diluted with EtOAc (350 ml). The organic phase was washed with aqueous HC1 (1 N),saturated aqueous sodium bicarbonate, and brine, then dried (Na2SO4) and concentrated in vacua. Theresulting solid was purified by flash silica gel chromatography, eluting with a gradient 0-4%EtOAc/hexanes. The resulting methyl 4-vinylbicyclo[2.2.2]octane-l-carboxylate (4-2) was isolated as aclear, colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; hexanes; at -78 - 20℃; for 0.5h; | To a suspension of methyltriphenylphosphonium bromide (1.76 g, 4.93 mmol) in THF (30 ml), cooled to -78 C., was added n-BuLi (1.88 ml of 2.5M soln. in hexanes; 4.68 mmol), and the mixture was stirred at -78 C. for 30 min and then at 0 C. for 45 min. It was cooled back to -78 C., and a solution of aldehyde 6 (0.50 g, 2.34 mmol) in THF (5 ml) was added. The reaction mixture was stirred at -78 C. for 30 min and warmed up to rt. It was quenched with water, and the product was extracted with CH2Cl2. The organic layer was dried over Na2SO4 and purified by flash chromatography (0.5% MeOH/CH2Cl2) to provide 0.24 g of 20 as a clear oil. Step 2: BOC-deprotection and amide coupling steps as described in Example 2 were used to obtain the title compound MS (M+H): 347. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; hexanes at -78 - 20℃; for 1h; | 17.a Step a) 1-Bromo-3-but-3-enylbenzene A solution of 1.34 gm (3.77 mmol) of methyltriphenylphosphonium bromide in THF at 0° C. was treated dropwise with 2.3 mL of 1.6 M n-BuLi in hexanes (3.77 mmol), stirred at 0° C. for 0.25 h, cooled to -78° C., treated dropwise with a solution of 3-(3-bromophenyl)propionaldehyde (0.7 gm, 3.28 mmol) in THF, stirred at -78° C. for 1 h, allowed to warm to room temperature, quenched with aqueous NH4Cl and concentrated under reduced pressure. The resultant residue was taken up in EtOAc, washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of this concentrate on silica gel with a gradient of 0.5% EtOAc-hexanes to 2.0% EtOAc-hexanes gave 1-bromo-3-but-3-enylbenzene as an oil, 0.35 gm (50% yield); 1H NMR (400 MHz, CDCl3) δ: 2.33 (m, 2H), 2.66 (t, 2H, J=7.4 Hz), 4.98 (m, 2H), 5.79 (m, 1H), 7.12 (m, 2H), 7.30 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 1h; | 13 Compound 4.; (Kuei-Ying Lin, Mark Matteucci US 5414077) A solution of potassium-t-butoxide (2.51 g, 22.3 mmol) in anhydrous THF (40 mL) was added to a suspension of methyltriphenylphosphonium bromide (7.99 g, 22.3 mmol) in THF (40 mL) at 0°C. The resulting yellow ylide suspension was stirred at 0°C for 2 h before the addition of the solution of N-BOC protected 4-oxo-L-proline methyl ester 3 (2.72 g, 11.2 mmol) in THF (32 mL). After stirring at rt for 1 h, the reaction mixture was diluted with EtOAc (100 mL), washed with H2O (80 mL), brine (80 mL), dried (MgSO4), and concentrated. Purification of the residue by flash chromatography (silica gel, 9:1 hexanes/EtOAc) yielded N-BOC protected 4-methylene-L-proline methyl ester, compound 4, as colorless oil: 1HNMR (300 MHz, CDCl3, rotamers) δ 1.40 and 1.45 (2 x s, 9H), 2.58 - 2.62 (m, 1 H), 2.88 - 2.98 (m, 1 H), 3.69 and 3.70 (2 x s, 3H), 4.03 - 4.06 (m, 2H), 4.36 - 4.49 (m, 1 H), 4.97 - 4.99 (m, 2H); EIMS m/z 264 ([M]++Na). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In 1,2-dimethoxyethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.5 g | In diethyl ether at 20℃; for 4h; | a To a stirred solution of ketoester B-21a (0.5 g, 2.291 mmol) in Et20 (5 mL) was added methylenetriphenylphosphorane (0.760 g, 2.75 mmol) portion-wise at room temperature and stirred for 4 h. The reaction was quenched with water (50 mL) and extracted with EtOAc (200 mL). The organic layer was dried over a2S04, filtered and evaporated under reduced pressure. The crude material was purified by flash chromatography (Silica gel 230-400, 5% EtOAc/petroleum ether) to give ester B-27a (0.5 g) as a pale yellow liquid.XH NMR (CDC13, δ = 7.26 ppm, 400 MHz): δ 7.38-7.29 (m, 5 H), 5.12 (s, 2 H), 4.94 -4.89 (m, 2 H), 1.88 (dd, J = 1.2, 0.8, 3 H), 1.37-1.35 (m, 2 H), 0.97-0.94 (m, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | Stage #1: 5-Methylindole-2-carboxaldehyde With potassium hexamethylsilazane In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: Methylenetriphenylphosphorane In tetrahydrofuran; hexane at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
129 mg | With di-tert-butyl peroxide; triphenylphosphine In hexane; dichloromethane; dimethyl sulfoxide at 20℃; for 12h; Irradiation; Inert atmosphere; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-tert-butyl peroxide; triphenylphosphine In hexane; dichloromethane; dimethyl sulfoxide at 20℃; for 12h; Irradiation; Inert atmosphere; Green chemistry; |
Tags: 19493-09-5 synthesis path| 19493-09-5 SDS| 19493-09-5 COA| 19493-09-5 purity| 19493-09-5 application| 19493-09-5 NMR| 19493-09-5 COA| 19493-09-5 structure
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