Name: 1100-88-5|Benzyltriphenylphosphonium chloride|98%
Brand: Ambeed
SKU: A147284
Rating: 98 (25 reviews)

1
[ 1100-88-5 ]
[ 7650-91-1 ]

Reference： [1]Chemische Berichte,1959,vol. 92,p. 2088,2093

2
[ 1100-88-5 ]
[ 16721-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; dimethyl sulfoxide; at 70℃;	Reference Example 21 (2S,4E)-4-benzylidene-N-(t-butoxycarbonyl)pyrrolidine-2-carboxylic acid To a suspension of sodium hydride (1.15 g) in DMSO (30 ml), a solution of <strong>[1100-88-5]benzyltriphenylphosphonium chloride</strong> (11.7 g) in DMSO (30 ml) was added. The mixture was stirred at 70 C. After the mixture became uniform, the mixture was cooled to room temperature. A solution of the compound prepared in Reference Example 20 (2.29 g) in DMSO (10 ml) was added dropwise to the mixture. The mixture was stirred for 3 hours at 70 C and overnight at room temperature. The reaction mixture was added to an iced aqueous solution of potassium hydrogen carbonate (2 g). After the mixture was washed with diethyl ether, the aqueous layer was acidified by adding 1 N hydrochloric acid and was extracted with ethyl acetate. The organic layer was concentrated. The residue was dissolved into 1N aqueous solution of sodium hydride. The mixture was washed with diethyl ether. The aqueous layer was acidified by adding 1 N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried and concentrated. The residue was dissolved in ethyl acetate and dicyclohexylamine was added to the mixture. The precipitate was obtained by filtration, washed with ethyl acetate and dried. Ethyl acetate and 1N hydrochloric acid were added to the obtained solid. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried and concentrated to give the title compound (1.20 g).
	With potassium tert-butylate; In 1,4-dioxane; at 20 - 80℃; for 1h;Inert atmosphere;	General procedure: An adapted method published by Giannis et al.5e was used: KOt- Bu (2 equiv) was added to a solution of the phosphonium compound (2 equiv) in dry 1,4-dioxane (carbohydrate concentration 0.2 M) and stirred at room temperature for 30 min. and then at 80 C for 30 min. Next, the carbohydrate (1 equiv) was added and the mixture was heated to reflux until full or no further conversion of the reaction was confirmed by TLC. The specific isolation of the products is described for the individual carbohydrates.
	With n-butyllithium; In tetrahydrofuran; hexane; at 0℃; for 1h;Inert atmosphere; Schlenk technique;	Benzyltriphenylphosphonium chloride (1.67 g, 4.29 mmol) was placed into a Schlenk flask, and 50 mL of absolute tetrahydrofuran was added. The obtained suspension was cooled to 0C, and 4.29 mmol of a 1.6 M n-BuLi solution in hexane was slowly added to it. The red-brown mixture was stirred at 0C for 1 h, and then a solution of 0.72 g (3.90 mmol) of 2-bromobenzaldehyde was slowly added to the mixture at this temperature. The mixture was stirred at room temperature for 24 h,50 mL of an aqueous solution of NaCl was added, and it was twice extracted with ethyl acetate; the combined organic phases were repeatedly washed with a solution of NaCl, and the aqueous phase was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, and the solvent was evaporated. The yellow solid residue was applied onto a column with silica gel (Acros, 60-200 mum), the colorless first fraction was eluted with hexane, and the solvent was evaporated.

Reference： [1]Russian Chemical Bulletin,2007,vol. 56,p. 2284 - 2289
[2]Patent: DE943648,1954,
[3]Journal of Organic Chemistry,1990,vol. 55,p. 360 - 363
[4]Journal of Organic Chemistry,1980,vol. 45,p. 4129 - 4135
[5]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 641 - 643
[6]Polish Journal of Chemistry,1988,vol. 62,p. 549 - 552
[7]Australian Journal of Chemistry,1988,vol. 41,p. 235 - 249
[8]Chemische Berichte,1986,vol. 119,p. 2466 - 2472
[9]Zeitschrift fur Naturforschung, B: Chemical Sciences,1988,vol. 43,p. 1293 - 1306
[10]Recueil des Travaux Chimiques des Pays-Bas,1995,vol. 114,p. 514 - 516
[11]Journal of Organic Chemistry,1993,vol. 58,p. 301 - 303
[12]Journal of Chemical Research, Miniprint,1996,p. 2361 - 2374
[13]Journal of the American Chemical Society,1997,vol. 119,p. 2832 - 2838
[14]Bulletin of the Chemical Society of Japan,2000,vol. 73,p. 2559 - 2562
[15]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598
[16]New Journal of Chemistry,2003,vol. 27,p. 1592 - 1598
[17]Synlett,2009,p. 1579 - 1582
[18]Patent: EP1535906,2005,A1 .Location in patent: Page/Page column 39-40
[19]Synlett,2010,p. 2257 - 2262
[20]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742
[21]Carbohydrate Research,2012,vol. 362,p. 30 - 37,8
[22]Magnetic Resonance in Chemistry,2016,vol. 54,p. 17 - 27
[23]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5023 - 5027
[24]Petroleum Chemistry,2020,vol. 60,p. 55 - 68
Neftekhimiya,2020,vol. 60,p. 61 - 75,15

3
[ 73291-09-5 ]
[ 1100-88-5 ]
[ 101095-61-8 ]

Reference： [1]Chemische Berichte,1961,vol. 94,p. 907 - 914

4
[ 872-85-5 ]
[ 1100-88-5 ]
[ 5097-92-7 ]
[ 5097-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Iseki, Yûki; Watanabe, Eishun; Mori, Atsunori; Inoue, Shohei [Journal of the American Chemical Society, 1993, vol. 115, # 16, p. 7313 - 7317]

5
[ 98-01-1 ]
[ 1100-88-5 ]
[ 1202-49-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Amberlite IR-400; In N,N-dimethyl-formamide; at 95℃; for 10h;Inert atmosphere;	General procedure: A round-bottom flask was charged with the suspension of ylide (1.5 mmol) in DMF (4 mL) and then Amberlite IR-400 (OH-) (1.2 g) was added to it. The content was stirred for the next 20 min at 95 C under inert atmosphere, then appropriate aldehyde (1 mmol) was added to the reaction mixture and heating was continued for next 10 h. On completion of the reaction (TLC [thin layer chromatography]), the resin was filtered off and the crude reaction mixture was evaporated to dryness. Isolation of the product was performed by flash chromatography (CombiFlash Rf 200i with UV/VIS and ELSD, Isco Teledyne Inc., USA) using RediSep column (SiO2). All the products were identified on the basis of their spectral data.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 581 - 589
[2]Collection of Czechoslovak Chemical Communications,1981,vol. 46,p. 515 - 519

6
[ 22720-75-8 ]
[ 1100-88-5 ]
[ 84258-69-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 871 - 877

7
[ 51234-09-4 ]
[ 1100-88-5 ]
[ 144412-67-9 ]
[ 144412-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate 1) ethanol, room temperature, 10 min, 2) ethanol, room temperature, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Meier, Herbert; Kretzschmann, Holger; Kolshorn, Heinz [Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6847 - 6852]

8
[ 1100-88-5 ]
[ 104-88-1 ]
[ 1657-49-4 ]
[ 1657-50-7 ]

Yield	Reaction Conditions	Operation in experiment
57%; 37%	With tetra-n-butylammonium 4-methyl-1-phenyl-2,6,7-trioxa-1-borabicyclo-[2.2.2]octan-1-uide; In dichloromethane; at 20℃;Inert atmosphere;	General procedure: To a round-bottom flask (25 mL), a phosphonium salt 6 (0.5 mmol), phenyltriolborate 4a (223.8 mg, 0.5 mmol), p-chlorobenzaldehyde (5a; 56.2 mg, 0.4 mmol), and CH2Cl2 (5 mL) were added. The mixture was stirred at r.t., and the reaction progress was monitored by TLC. After reaction completion, the reaction mixture was concentrated and separated by preparative TLC (silica gel) to afford the olefination product.

Reference： [1]Synthesis,2015,vol. 47,p. 359 - 366
[2]Journal of the Chemical Society. Perkin transactions II,1981,p. 324 - 326
[3]Chemistry - A European Journal,2002,vol. 8,p. 2568 - 2573
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2007,vol. 46,p. 370 - 374
[5]Chemistry - A European Journal,2011,vol. 17,p. 8794 - 8798
[6]Journal of Organic Chemistry,2016,vol. 81,p. 7799 - 7806

9
[ 1100-88-5 ]
[ 1442-03-1 ]
[ 113195-49-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2455 - 2460

10
[ 1100-88-5 ]
[ 25711-30-2 ]
[ 77219-17-1 ]

Reference： [1]Journal of general chemistry of the USSR,1980,vol. 50,p. 1922 - 1926
Zhurnal Obshchei Khimii,1980,vol. 50,p. 2370 - 2375

11
[ 1100-88-5 ]
[ 459-57-4 ]
[ 718-25-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of benzyl chloride(0.126 g, 1.00 mmol) in dry toluene (7 mL), was added triphenylphosphine(0.313 g, 1.20 mmol) at ambient temperature. Thereaction mixture was allowed to reflux for 18 h under N2 atmosphere;during this time the Wittig salt precipitated out, it was filtered,washed and used for further reaction. To a solution of Wittigsalt (0.08 g, 0.20 mmol) in CH2Cl2, was added NaOH solution(0.01 g, 0.25 mmol, 3 mL water) at ambient temperature. The solutionturned orange red indicating the formation of Wittig ylide. Tothis solution was added benzaldehyde (0.018 g, 0.16 mmol) andthe reaction mixture allowed to stir at ambient temperature for3 h. The crude product formed was extracted with CH2Cl2, washedwith brine and evaporated to dryness. After usual column chromatography(hexane: EtOAc; 9:1), the product obtained was a mixtureof cis and trans-isomer, isolated in 87% yield. The abovemixture was dissolved in hexane containing catalytic amount ofiodine and allowed to reflux for 1 h. The reaction mixture wascooled down to ambient temperature, washed with Na2S2O5 solutionand the organic layer evaporated to give pure trans-isomer (1)in quantitative yield (89%).

Reference： [1]Archiv der Pharmazie,1995,vol. 328,p. 595 - 603
[2]Bioorganic Chemistry,2016,vol. 64,p. 97 - 102

12
[ 7089-68-1 ]
[ 1100-88-5 ]
[ 163231-36-5 ]

Reference： [1]Journal of Physical Chemistry,1996,vol. 100,p. 16175 - 16186

13
[ 329-98-6 ]
[ 1100-88-5 ]
[ 51848-91-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 875 - 880

14
[ 1100-88-5 ]
[ 313950-41-3 ]
[ 313950-42-4 ]

Reference： [1]Organic letters,2000,vol. 2,p. 3679 - 3681

15
[ 1100-88-5 ]
[ 276699-71-9 ]
[ 276699-72-0 ]

Reference： [1]Organic letters,2000,vol. 2,p. 3679 - 3681

16
[ 1100-88-5 ]
[ 193480-28-3 ]
[ 313950-43-5 ]

Reference： [1]Organic letters,2000,vol. 2,p. 3679 - 3681

17
[ 1100-88-5 ]
[ 1122-91-4 ]
[ 4714-24-3 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of benzyl chloride (0.126 g, 1.00 mmol) in dry toluene (7 mL), was added triphenylphosphine (0.313 g, 1.20 mmol) at ambient temperature. The reaction mixture was allowed to reflux for 18 h under N2 atmosphere; during this time the Wittig salt precipitated out, it was filtered, washed and used for further reaction. To a solution of Wittig salt (0.08 g, 0.20 mmol) in CH2Cl2, was added NaOH solution (0.01 g, 0.25 mmol, 3 mL water) at ambient temperature. The solution turned orange red indicating the formation of Wittig ylide. To this solution was added benzaldehyde (0.018 g, 0.16 mmol) and the reaction mixture allowed to stir at ambient temperature for 3 h. The crude product formed was extracted with CH2Cl2, washed with brine and evaporated to dryness. After usual column chromatography (hexane: EtOAc; 9:1), the product obtained was a mixture of cis and trans-isomer, isolated in 87% yield. The above mixture was dissolved in hexane containing catalytic amount of iodine and allowed to reflux for 1 h. The reaction mixture was cooled down to ambient temperature, washed with Na2S2O5 solution and the organic layer evaporated to give pure trans-isomer (1) in quantitative yield (89%)

Reference： [1]Journal of Physical Organic Chemistry,2012,vol. 25,p. 597 - 606
[2]Bioorganic Chemistry,2016,vol. 64,p. 97 - 102

18
[ 694-54-2 ]
[ 1100-88-5 ]
[ 98078-15-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: benzyltriphenylphosphonium chloride With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 20℃; for 0.5h; Stage #2: tetrahydro-2H-2-pyranol In <i>tert</i>-butyl alcohol at 20℃; for 0.5h;

Reference： [1]Tamura, Osamu; Mitsuya, Takahiro; Huang, Xin; Tsutsumi, Yoshiyuki; Hattori, Sanae; Ishibashi, Hiroyuki [Journal of Organic Chemistry, 2005, vol. 70, # 26, p. 10720 - 10725]

19
[ 2142-06-5 ]
[ 1100-88-5 ]
(5E)-1-benzyl-5-benzylidenepyrrolidin-2-one [ No CAS ]

Reference： [1]Heterocyclic Communications,2006,vol. 12,p. 179 - 182

20
[ 1100-88-5 ]
[ 39229-12-4 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1995,vol. 101,p. 281 - 286

21
[ 1100-88-5 ]
[ 791-28-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With water; sodium hydroxide at 20℃;	General procedure for alkaline hydrolysis of phosphonium salts or phosphorus ylides in 3 M NaOH General procedure: To a round-bottom flask (5 mL) containing phosphonium salt 1 or ylide 3 or 4 (0.5 mmol), 3 M NaOH (2 mL) was added. The resulting mixture was stirred at room temperature (1a, 1h, 1i, overnight; 1c, 3 h) or refluxed for 3-10 h (1b, 1d, 1e, 4, 3 h; 1f, 5 h; 1g, 10 h) till the phosphonium salt or ylide was consumed as monitored by TLC. Then the mixture was extracted with EtOAc (10 mL x 3), and the combined extract was evaporated to remove the solvent. The residue was dried in vacuo or further isolated by column chromatography or preparative TLC to give phosphine oxides 2 or Ph3PO.
	Multi-step reaction with 2 steps 1: 1.) BuLi / 1) THF, hexane, room temperature, 30 min; 2) THF, hexane, room temperature, 3 h 2: 1 h / 850 °C / 0 - 0.01 Torr
	Multi-step reaction with 2 steps 1: 1.) BuLi / 1) THF, hexane, room temperature, 30 min; 2) THF, hexane, room temperature, 3 h 2: 1 h / 850 °C / 0 - 0.01 Torr

Multi-step reaction with 3 steps 1: NaH, Dimethylsulfoxide 2: 60 percent / dimethylsulfoxide / 0.5 h / Ambient temperature 3: 0.03 h / 180 °C

Reference： [1]Zhong, Chun-Hong; Huang, Wenhua [Synthetic Communications, 2021, vol. 51, # 10, p. 1537 - 1546]
[2]Aitken, R. Alan; Burns, Graham [Journal of the Chemical Society. Perkin transactions I, 1994, # 17, p. 2455 - 2460]
[3]Aitken, R. Alan; Burns, Graham [Journal of the Chemical Society. Perkin transactions I, 1994, # 17, p. 2455 - 2460]
[4]Compagini, Anna; Lo Vullo, Adriana; Chiacchio, Ugo; Corsaro, Antonio; Purrello, Giovanni [Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 641 - 643]

22
N-2,2,2-trichloroethoxycarbonyltropinone [ No CAS ]
[ 1100-88-5 ]
8-(2,2,2-Trichloroethoxycarbonyl)-3-phenyl-methylene-8-azabicyclo[3.2.1]octane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With n-butyllithium; In tetrahydrofuran; hexane; ethyl acetate;	PREPARATION 1 8-(2,2,2-Trichloroethoxycarbonyl)-3-phenylmethylene-8-azabicyclo[3.2.1.]octane A solution of <strong>[1100-88-5]benzyltriphenylphosphonium chloride</strong> (13.26 g, 34.1 mmol) in tetrahydrofuran (400 ml) was chilled to -78 C. and butyl lithium (13.6 ml of 2.5M in hexanes, 34 mmol) was added. This resulted in a heterogeneous orange mixture which was stirred 5 minutes at -78 C. and then warmed to 0 C. The solution became nearly homogeneous red and N-2,2,2-trichloroethoxycarbonyltropinone (7.1 g, 23.3 mmol; Montzka et al., Tetrahedron Letters, vol, 14, p. 1325, 1974) was added in tetrahydrofuran (20 ml with a 20 ml rinse). The reaction was refluxed 4 days, cooled, and filtered. Concentration of the filtrate left a viscous brown oil. Flash chromatography on silica gel (3*6 inches) using first hexane and then an ethylacetate/hexane gradient gave 7.87 g of white solid product (74%); mp 88-89 C., ir (KBr) 3437, 2958, 1700, 1445, 1425, 1321, 1125, 711. Anal. C 54.89, H 4.82, N 3.77, calcd. C 54.49, H 4.84, N 3.74.

Reference： [1]Patent: US5185343,1993,A

23
[ 1100-88-5 ]
[ 170491-66-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	In ethanol; pentane;	Stage a) In a reactor protected from moisture, there are introduced 180 ml of absolute ethanol, followed, with stirring, by 1.63 g (0.071 mol) of scraped sodium. After dissolution, at 20-25 C., 27.3 g (0.071 mol) of <strong>[1100-88-5]benzyltriphenylphosphonium chloride</strong> are added. The yellowish suspension is kept stirring for 30 min at 20-25 C. and a solution of 16.0 g (0.070 mol) of the previously obtained acetaldehyde (formula VI; n=2) in 35 ml of absolute ethanol is then introduced during approximately 2 min. The white solution obtained is maintained for 30 minutes at 20-25 C. and the insoluble matter is filtered out on a Buchner funnel and discarded. The filtrate is evaporated under vacuum and on a water bath. The oily residue is solidified in 500 ml of n-pentane, and this new insoluble matter is filtered out and removed. The filtrate is concentrated. 19.0 g of crude N-t-butyloxycarbonyl-(2-cinnamyl)piperidine are obtained (formula V; Z=t-butyl, Ar=C6 H5, n=2) (yield=90%) and are introduced in the next stage without further treatment.

Reference： [1]Patent: US5849760,1998,A

24
[ 2386-60-9 ]
[ 1100-88-5 ]
[ 660-12-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride In water	23 EXAMPLE 23 EXAMPLE 23 A mixture consisting of 156.6 g (1 mol) of n-butanesulphonic acid chloride and a solution of 69.6 g (1.2 mols) of potassium fluoride in 160 ml of water is treated with 10 g of triphenylbenzylphosphonium chloride. After stirring for 3 hours at room temperature, the crude n-butanesulphonic acid fluoride is separated off and subjected to fractional distillation. This gives 122 g (87% of theory) of n-butanesulphonic acid fluoride (boiling point10: 45 - 48° C).

Reference： [1]Current Patent Assignee: BAYER AG - US4060549, 1977, A

25
[ 1100-88-5 ]
1-Phenyl-3,3,3-trifluoro-2-(4-fluorophenyl)-propene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium ethanolate; In ethanol;	1-[4-(2-Bromoethoxy)-phenyl]-1-phenyl-3,3,3-trifluoro-2-(4-fluorophenyl)-propene, applied as starting substance, is prepared by the method of Examples 1 and 7 as follows: 4'-Fluoro-2,2,2-trifluoroacetophenone (F. E. Herkes et al.: J. Org. Chem. 32, 1311-18 (1967)) is reacted with benzyl-triphenyl-phosphonium chloride in the presence of an ethanol solution of sodium ethoxide. 1-Phenyl-3,3,3-trifluoro-2-(4-fluorophenyl)-propene is obtained with a yield of 91%; b.p.: 110-114 C./0.2 mm Hg, m.p.: 43-45 C. Analysis: calculated for C15 H10 F4: C: 67.67%, H: 3.79%, F: 28.54%; found: C: 67.83%, H: 3.90%, F: 28.33%.

Reference： [1]Patent: US4806685,1989,A

26
[ 10170-68-0 ]
[ 53348-04-2 ]
[ 1100-88-5 ]
[ 143252-32-8 ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1992,p. 1803 - 1812

27
[ 1018124-86-1 ]
[ 1100-88-5 ]
1,3-diphenyl-2-bis(2-methoxyethyl)aminomethylpropene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 4140 - 4145

28
[ 1100-88-5 ]
[ 79099-07-3 ]
[ 209920-41-2 ]

Yield	Reaction Conditions	Operation in experiment
90%		[0520] To a suspension of <strong>[1100-88-5]benzyltriphenylphosphonium chloride</strong> (2.24 g, 5.76 mmol) was added n-BuLi (2.3M in hexanes, 3.0 mL, 6.9 mmol) at 0 C. The mixture was allowed to stir for 30 min, after which time it had become a deep red solution. To this was added N-Boc-4-piperidone (0.748 g, 6.05 mmol) and the solution was stirred at room temperature for 48 hours. The reaction was quenched with NH4Cl and extracted with EtOAc (×2). The combined organic layers were washed, (H2O, brine) and dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (SiO2/hexane-EtOAc, 4:1) to afford the product (1.41 g, 90%) as a colourless liquid which solidified on standing: [0521] 1Hnmr (400 MHz, CDCl3) delta 7.33-7.29, (m, 2H), 7.17-7.21 (m, 3H), 6.35 (s, 1H), 3.50 (t, J=5.8 Hz, 2H), 3.39 (t, J=5.5 Hz, 2H), 2.45 (t, J=5.5 Hz, 2H), 2.32 (app t, J=5.3, 5.6 Hz, 2H), 1.47 (s, 9H).

Reference： [1]Patent: US2004/63744,2004,A1 .Location in patent: Page/Page column 102

29
[ 1100-88-5 ]
[ 555-16-8 ]
[ 1694-20-8 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of benzyl chloride (0.126 g, 1.00 mmol) in dry toluene (7 mL), was added triphenylphosphine (0.313 g, 1.20 mmol) at ambient temperature. The reaction mixture was allowed to reflux for 18 h under N2 atmosphere; during this time the Wittig salt precipitated out, it was filtered, washed and used for further reaction. To a solution of Wittig salt (0.08 g, 0.20 mmol) in CH2Cl2, was added NaOH solution (0.01 g, 0.25 mmol, 3 mL water) at ambient temperature. The solution turned orange red indicating the formation of Wittig ylide. To this solution was added benzaldehyde (0.018 g, 0.16 mmol) and the reaction mixture allowed to stir at ambient temperature for 3 h. The crude product formed was extracted with CH2Cl2, washed with brine and evaporated to dryness. After usual column chromatography (hexane: EtOAc; 9:1), the product obtained was a mixture of cis and trans-isomer, isolated in 87% yield. The above mixture was dissolved in hexane containing catalytic amount of iodine and allowed to reflux for 1 h. The reaction mixture was cooled down to ambient temperature, washed with Na2S2O5 solution and the organic layer evaporated to give pure trans-isomer (1) in quantitative yield (89%)

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 10013 - 10021
[2]Bioorganic Chemistry,2016,vol. 64,p. 97 - 102

30
[ 1164123-81-2 ]
[ 1100-88-5 ]
[ 1164123-82-3 ]

Yield	Reaction Conditions	Operation in experiment
93%		Step B: Preparation of tert-Butyl-(5-phenylethylene-pyridin-3-yl)-3, 6-diazabicyclo[3.2.1]octane-3-carboxylateTo a solution of benzyl triphenylphosphonium chloride (169 mg, 0.422 mmol) in 4 mL dry THF was added a solution of sodium hexamethyldisilazide (0.461 mL of 1 N, 0.461 mmol), and the resulting solution stirred 45 min. at 400C. To the resulting solution was added a solution of tert-butyl-(5- carboxaldehydo-pyridin-3-yl)-3,6-diazabicyclo[3.2.1]octane-3-carboxylate (122 mg, 0.382 mmol) in 1 mL dry THF. The reaction was stirred at 50-600C for 24 hr., and the reaction cooled, taken up in EtOAc, washed with water and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel to afford the product, 141 mg (93%), as an oil, a mixture of olefin isomers. 13C NMR (100MHz, CDCI3) delta 28.70, 28.78, 32.87, 33.02, 33.15, 33.60, 33.73, 33.86, 34.16, 34.40, 34.48, 50.34, 50.46, 50.77, 50.81, 50.88, 50.97, 51.24, 51.40, 52.09, 52.21, 52.32, 52.51 , 52.65, 52.88, 79.66, 79.76, 79.92, 115.97, 116.24, 116.41, 116.94, 119.36, 125.77, 125.93, 126.78, 127.33, 127.61, 128.20, 128.63, 128.75, 128.86, 128.94, 130.40, 130.90, 130.99, 131.52, 131.79, 132.12, 132.14, 132.21 , 132.31 , 132.73, <n="73"/>132.86, 133.08, 133.24, 134.16, 134.28, 134.86, 134.96, 137.01, 138.23, 138.30, 139.12, 139.58, 139.80, 140.69, 141.63, 142.03, 146.39, 154.13; LCMS (m/z) 392 (M+H). RT (Method A, supra), 1.0 min.

Reference： [1]Patent: WO2009/81246,2009,A2 .Location in patent: Page/Page column 70; 71

31
[ 349-75-7 ]
[ 1100-88-5 ]
[ 891-70-3 ]
(Z)-1-(3-trifluoromethylphenyl)-2-phenylethene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 6034 - 6042

32
[ 19005-93-7 ]
[ 1100-88-5 ]
[ 60986-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium ethoxide; In ethanol; at 20℃;	[00248] 2-Styryl-lH-indole. To a solution of tetraphenylphosphonium chloride (1.34 g,3.44 mmol) and lH-indole-2-carbaldehyde (500 mg, 3.44 mmol) in anhydrous EtOH (10 ml) was added IM LiOEt in EtOH (3.5 ml, 3.44 mmol) at room temperature. The mixture was stirred at room temperature overnight, quenched with water and extracted with ethyl acetate. The combined organic extract was washed with brine, dried over N32So4 and evaporated under reduced pressure. The crude product was purified by preparative TLC (silica gel, hexane/ethyl acetate) to afford 2-styryl-lH-indole. MS (ES+): m/z 220.13 (MH+).

Reference： [1]Patent: WO2010/68287,2010,A2 .Location in patent: Page/Page column 112
[2]Chemistry - A European Journal,2010,vol. 16,p. 5853 - 5857

33
[ 69610-41-9 ]
[ 1100-88-5 ]
[ 220510-68-9 ]

Yield	Reaction Conditions	Operation in experiment
40%		Benzyltriphenylphosphonium chloride (3.89 g, 10 mmol) in 10 mL diethyl ether was placed in a round bottom flask. The solution was cooled to -780C and «BuLi (4 mL of 2.5M nBuLi in hexane, 10 mmol) was added dropwise to the solution. After 30 min, the suspension was added dropwise to l-tBoc-2-formyl pyrrolidine (2 g, 10 mmol) in 10 mL diethyl ether at -78C and the mixture was stirred for 3 hours. The reaction was stopped with 50 mL H2O, the organic layer was separated from the aqueous layer, and the aqueous layer was extracted 3 times with 50 mL diethyl ether. The combined organic layer was washed with H2O until the pH of the aqueous layer was 7, dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica column chromatography EtOAc/ hexane (10:90, v:v), 1.1 g, 40% yield.

Reference： [1]Patent: WO2006/25920,2006,A2 .Location in patent: Page/Page column 57-58

34
[ 155494-81-8 ]
[ 1100-88-5 ]
[ 1293365-18-0 ]

Yield	Reaction Conditions	Operation in experiment
80%		The appropriate 2-aroyl-3,3-bis(alkylthio)acrylaldehyde (1 mmol) dissolved in DCM (15 mL) was stirred with triphenylbenzyl phosphonium chloride (0.39 g, 1 mmol) for 5 min at room temperature. To this was added 50% aqueous NaOH (7.5 mL) solution slowly and the mixture was stirred further for 1 h at room temperature. The reaction mixture was then poured onto ice-cold water (20 mL). A semi-solid obtained was extracted with DCM (3 × 25 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated off. The crude product obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate-hexane (1:19) mixture as the eluent to get 2a-g in 78-90% yield as pale yellow crystalline solid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1667 - 1669

35
[ 1293365-15-7 ]
[ 1100-88-5 ]
[ 1293365-20-4 ]

Yield	Reaction Conditions	Operation in experiment
82%		The appropriate 2-aroyl-3,3-bis(alkylthio)acrylaldehyde (1 mmol) dissolved in DCM (15 mL) was stirred with triphenylbenzyl phosphonium chloride (0.39 g, 1 mmol) for 5 min at room temperature. To this was added 50% aqueous NaOH (7.5 mL) solution slowly and the mixture was stirred further for 1 h at room temperature. The reaction mixture was then poured onto ice-cold water (20 mL). A semi-solid obtained was extracted with DCM (3 × 25 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated off. The crude product obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate-hexane (1:19) mixture as the eluent to get 2a-g in 78-90% yield as pale yellow crystalline solid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1667 - 1669

36
[ 1100-88-5 ]
[ 134129-19-4 ]
[ 34631-59-9 ]

Yield	Reaction Conditions	Operation in experiment
83%		The appropriate 2-aroyl-3,3-bis(alkylthio)acrylaldehyde (1 mmol) dissolved in DCM (15 mL) was stirred with triphenylbenzyl phosphonium chloride (0.39 g, 1 mmol) for 5 min at room temperature. To this was added 50% aqueous NaOH (7.5 mL) solution slowly and the mixture was stirred further for 1 h at room temperature. The reaction mixture was then poured onto ice-cold water (20 mL). A semi-solid obtained was extracted with DCM (3 × 25 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated off. The crude product obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate-hexane (1:19) mixture as the eluent to get 2a-g in 78-90% yield as pale yellow crystalline solid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1667 - 1669

37
[ 1100-88-5 ]
[ 134129-40-1 ]
[ 1293365-21-5 ]

Yield	Reaction Conditions	Operation in experiment
78%		The appropriate 2-aroyl-3,3-bis(alkylthio)acrylaldehyde (1 mmol) dissolved in DCM (15 mL) was stirred with triphenylbenzyl phosphonium chloride (0.39 g, 1 mmol) for 5 min at room temperature. To this was added 50% aqueous NaOH (7.5 mL) solution slowly and the mixture was stirred further for 1 h at room temperature. The reaction mixture was then poured onto ice-cold water (20 mL). A semi-solid obtained was extracted with DCM (3 × 25 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated off. The crude product obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate-hexane (1:19) mixture as the eluent to get 2a-g in 78-90% yield as pale yellow crystalline solid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1667 - 1669

38
[ 1100-88-5 ]
[ 138696-49-8 ]
[ 1293365-19-1 ]

Yield	Reaction Conditions	Operation in experiment
86%		The appropriate 2-aroyl-3,3-bis(alkylthio)acrylaldehyde (1 mmol) dissolved in DCM (15 mL) was stirred with triphenylbenzyl phosphonium chloride (0.39 g, 1 mmol) for 5 min at room temperature. To this was added 50% aqueous NaOH (7.5 mL) solution slowly and the mixture was stirred further for 1 h at room temperature. The reaction mixture was then poured onto ice-cold water (20 mL). A semi-solid obtained was extracted with DCM (3 × 25 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated off. The crude product obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate-hexane (1:19) mixture as the eluent to get 2a-g in 78-90% yield as pale yellow crystalline solid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1667 - 1669

39
[ 1100-88-5 ]
[ 137621-83-1 ]
[ 1293365-17-9 ]

Yield	Reaction Conditions	Operation in experiment
85%		The appropriate 2-aroyl-3,3-bis(alkylthio)acrylaldehyde (1 mmol) dissolved in DCM (15 mL) was stirred with triphenylbenzyl phosphonium chloride (0.39 g, 1 mmol) for 5 min at room temperature. To this was added 50% aqueous NaOH (7.5 mL) solution slowly and the mixture was stirred further for 1 h at room temperature. The reaction mixture was then poured onto ice-cold water (20 mL). A semi-solid obtained was extracted with DCM (3 × 25 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated off. The crude product obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate-hexane (1:19) mixture as the eluent to get 2a-g in 78-90% yield as pale yellow crystalline solid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1667 - 1669

40
[ 1100-88-5 ]
[ 137621-81-9 ]
[ 1293365-16-8 ]

Yield	Reaction Conditions	Operation in experiment
90%		The appropriate 2-aroyl-3,3-bis(alkylthio)acrylaldehyde (1 mmol) dissolved in DCM (15 mL) was stirred with triphenylbenzyl phosphonium chloride (0.39 g, 1 mmol) for 5 min at room temperature. To this was added 50% aqueous NaOH (7.5 mL) solution slowly and the mixture was stirred further for 1 h at room temperature. The reaction mixture was then poured onto ice-cold water (20 mL). A semi-solid obtained was extracted with DCM (3 × 25 mL), the organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated off. The crude product obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate-hexane (1:19) mixture as the eluent to get 2a-g in 78-90% yield as pale yellow crystalline solid.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1667 - 1669

41
[ 6072-57-7 ]
[ 1100-88-5 ]
[ 1354727-76-6 ]