Name: 62784-66-1|Di(naphthalen-1-yl)methanol|98%
Brand: Ambeed
SKU: A756348
Price: 15.0 USD
Availability: InStock
Rating: 96 (40 reviews)

1
[ 62784-66-1 ]
[ 607-50-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With chloro-trimethyl-silane; sodium iodide In dichloromethane; acetonitrile at 0℃; for 1.5h; Inert atmosphere;
	With hydrogenchloride; hydrogen iodide; tin(ll) chloride weitere Reagenzien: Essigsaeure und CO₂;
	With hydrogenchloride; acetic acid; zinc

	With hydrogen iodide; acetic acid
	With hydrogen iodide; acetic acid
	With sodium tetrahydroborate; trifluoroacetic acid

Reference： [1]Roy, Avijit; Oestreich, Martin [Chemistry - A European Journal, 2021, vol. 27, # 32, p. 8273 - 8276]
[2]Wanscheidt; Moldawsski [Zhurnal Obshchei Khimii, 1931, vol. 1, p. 304,305, 316][Chemisches Zentralblatt, 1931, vol. 102, # II, p. 3208]
[3]Tschitschibabin; Magidson [Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2> 90, p. 170]
[4]Tschitschibabin [Chemische Berichte, 1911, vol. 44, p. 442]
[5]Blicke [Journal of the American Chemical Society, 1927, vol. 49, p. 2848]
[6]Gribble,G.W. et al. [Synthesis, 1977, p. 172 - 176]

2
[ 62784-66-1 ]
[ 605-78-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With nickel(II) triflate; cyclohexanone; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 110℃; for 12h; Schlenk technique;
60%	With chromic acid In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
	With chromic acid

With pyridinium chlorochromate In dichloromethane

Reference： [1]Ye, Danfeng; Liu, Zhiyuan; Sessler, Jonathan L.; Lei, Chuanhu [Chemical Communications, 2020, vol. 56, # 79, p. 11811 - 11814]
[2]Tartaglia, Sabina; Pace, Francesca; Scafato, Patrizia; Rosini, Carlo [Organic Letters, 2008, vol. 10, # 16, p. 3421 - 3424]
[3]Bauer [Chemische Berichte, 1909, vol. 42, p. 2589] Tschitschibabin [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 1031][Journal fuer Praktische Chemie (Leipzig), 1911, vol. <2> 84, p. 769]
[4]Bauer [Chemische Berichte, 1909, vol. 42, p. 2589]
[5]Assadi, Naela; Pogodin, Sergey; Cohen, Shmuel; Agranat, Israel [Structural Chemistry, 2012, vol. 23, # 3, p. 771 - 790,20]

3
[ 62784-66-1 ]
[ 239-60-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With phosphoric acid In water at 180℃; for 3h;
42%	at 180℃; for 6h;
	With phosphoric acid

	With succinic acid anhydride at 170 - 190℃;
	With hydrogenchloride; acetic acid; zinc
	With hydrogenchloride; acetic acid; zinc
	With meta-phosphoric acid at 174.85℃;
	With phosphoric acid

Reference： [1]Ghase, Vaijayanti D.; Hasija, Deepika C.; Patil, Vishwanath R.; Rananaware, Meenakshi M. [Polymer, 2020, vol. 209]
[2]Lin, Fei; Wang, Xingbao; Pan, Yupeng; Wang, Meiyan; Liu, Bo; Luo, Yi; Cui, Dongmei [ACS Catalysis, 2016, vol. 6, # 1, p. 176 - 185]
[3]Magidson [Chemische Berichte, 1925, vol. 58, p. 439]
[4]Tschitschibabin; Magidson [Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2> 90, p. 170] Tschitschibabin; Magidson [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 1393][Chemisches Zentralblatt, 1915, vol. 86, # I, p. 1123]
[5]Tschitschibabin; Magidson [Journal fur praktische Chemie (Leipzig 1954), 1914, vol. <2> 90, p. 170] Tschitschibabin; Magidson [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 1393][Chemisches Zentralblatt, 1915, vol. 86, # I, p. 1123]
[6]Schmidlin; Massini [Chemische Berichte, 1909, vol. 42, p. 2381]
[7]Morris, David G.; Higgins, Sean; Ryder, Karl S.; Howie, R. Alan; Muir, Kenneth W. [Acta Crystallographica, Section C: Crystal Structure Communications, 2000, vol. 56, # 5, p. 570 - 571]
[8]Tian, Yi; Uchida, Kazuyuki; Kurata, Hiroyuki; Hirao, Yasukazu; Nishiuchi, Tomohiko; Kubo, Takashi [Journal of the American Chemical Society, 2014, vol. 136, # 36, p. 12784 - 12793]

4
[ 62784-66-1 ]
[ 5467-20-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With phosphorus tribromide In dichloromethane at 0 - 20℃; for 15h;	Bis(1-naphthyl)methyl bromide (2c): Bis(1-naphthyl)methanol8 (1.7 g, 6 mmol) was dissolved in dichloromethane (60 mL). Phosphorous tribromide (0.28 mL, 3 mmol) was added slowly at 0 °C and the solution was allowed to warm to room temperature. The reaction was stirred at room temperature overnight after which water was added. The aqueous layer was extracted twice with dichloromethane. The combined organic fractions were dried over sodium sulfate and filtered on basic alumina. The solvent was removed in vacuo to afford the product as a white solid (1.87 g, 90 %).
71%	With phosphorus tribromide In dichloromethane at 0 - 20℃;
	With hydrogen bromide; acetic acid

Reference： [1]Holtz-Mulholland, Michael; Collins, Shawn K. [Synthesis, 2014, vol. 46, # 3, p. 375 - 380]
[2]Zhang, Jun; Gholami, Hadi; Ding, Xinliang; Chun, Minji; Vasileiou, Chrysoula; Nehira, Tatsuo; Borhan, Babak [Organic Letters, 2017, vol. 19, # 6, p. 1362 - 1365]
[3]Tschitschibabin [Chemische Berichte, 1911, vol. 44, p. 442]

5
[ 90-11-9 ]
[ 109-94-4 ]
[ 62784-66-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 1h;
93%	Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 65℃; for 2h; Inert atmosphere; Stage #2: formic acid ethyl ester In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Heating;
90%	Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 20℃; for 2.15h; Stage #2: formic acid ethyl ester In tetrahydrofuran at 20℃; for 2h;

90%	Stage #1: 1-Bromonaphthalene With iodine; magnesium In tetrahydrofuran at 20℃; for 2.25h; Stage #2: formic acid ethyl ester In tetrahydrofuran for 2h;
75%	Stage #1: 1-Bromonaphthalene With magnesium In tetrahydrofuran for 2h; Stage #2: formic acid ethyl ester In tetrahydrofuran at 20℃; for 2h;
	With n-butyllithium

Reference： [1]Kato, Kenichi; Furukawa, Ko; Mori, Tadashi; Osuka, Atsuhiro [Chemistry - A European Journal, 2018, vol. 24, # 3, p. 572 - 575]
[2]Roy, Avijit; Oestreich, Martin [Chemistry - A European Journal, 2021, vol. 27, # 32, p. 8273 - 8276]
[3]Zhang, Jun; Gholami, Hadi; Ding, Xinliang; Chun, Minji; Vasileiou, Chrysoula; Nehira, Tatsuo; Borhan, Babak [Organic Letters, 2017, vol. 19, # 6, p. 1362 - 1365]
[4]Zhang, Jun; Sheng, Wei; Gholami, Hadi; Nehira, Tatsuo; Borhan, Babak [Chirality, 2018, vol. 30, # 2, p. 141 - 146]
[5]Location in patent: experimental part Bassas, Oriol; Huuskonen, Juhani; Rissanen, Kari; Koskinen, Ari M.P. [European Journal of Organic Chemistry, 2009, # 9, p. 1340 - 1351]
[6]Morris, David G.; Higgins, Sean; Ryder, Karl S.; Howie, R. Alan; Muir, Kenneth W. [Acta Crystallographica, Section C: Crystal Structure Communications, 2000, vol. 56, # 5, p. 570 - 571]
[7]Tian, Yi; Uchida, Kazuyuki; Kurata, Hiroyuki; Hirao, Yasukazu; Nishiuchi, Tomohiko; Kubo, Takashi [Journal of the American Chemical Society, 2014, vol. 136, # 36, p. 12784 - 12793]

6
[ 90-11-9 ]
[ 66-77-3 ]
[ 62784-66-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 1-Bromonaphthalene With magnesium In diethyl ether Inert atmosphere; Stage #2: 1-naphthaldehyde In diethyl ether at 20℃; Inert atmosphere;
	With iodine; magnesium In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;
	With magnesium In tetrahydrofuran Heating;

Reference： [1]Tartaglia, Sabina; Pace, Francesca; Scafato, Patrizia; Rosini, Carlo [Organic Letters, 2008, vol. 10, # 16, p. 3421 - 3424]
[2]Liu, Bin; Song, Runjiang; Xu, Jun; Majhi, Pankaj Kumar; Yang, Xing; Yang, Song; Jin, Zhichao; Chi, Yonggui Robin [Organic Letters, 2020, vol. 22, # 9, p. 3335 - 3338]
[3]Ghase, Vaijayanti D.; Hasija, Deepika C.; Patil, Vishwanath R.; Rananaware, Meenakshi M. [Polymer, 2020, vol. 209]

7
[ 492-37-5 ]
[ 62784-66-1 ]
[ 1116086-42-0 ]
[ 7782-24-3 ]
[ 7782-26-5 ]

Yield	Reaction Conditions	Operation in experiment
36%	With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate;	Entry 16To a dichloromethane solution (1.5 mL) containing p-methoxybenzoic anhydride (103.0 mg, 0.360 mmol) and racemic 2-phenylpropionic acid (45.1 mg, 0.300 mmol); diisopropylethylamine (94.0 muL, 0.540 mmol), benzotetramisole (3.8 mg, 0.015 mmol), and 1,1-di(1-naphthyl)methanol (42.8 mg, 0.151 mmol) were added in order at room temperature. After stirring the reaction mixture solution at room temperature for 12 hr, the reaction was stopped with saturated ammonium chloride water. After fractionating the organic layer, the aqueous layer was extracted 4 times with diethyl ether. After combining the organic layers, they were dried with anhydrous sodium sulfate. After filtering the solution, it was vacuum concentrated, and the obtained mixture was fractionated by thin layer silica gel chromatography to obtain the corresponding optically active ester (45.0 mg, 36%, 91% ee) and a part of the unreacted optically active carboxylic acid. Then 1 M hydrochloric acid was added to the water layer, and after adjusting the pH to 2, extraction was carried out 4 times with diethyl ether. After-treatment was carried out in the same way as above, and unreacted optically active carboxylic acid was further recovered, and added to the previously obtained optically active carboxylic acid (17.5 mg, 39%, 52% ee).; di-(1-naphthyl)methyl (R)-2-phenylpropanoateHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/50, flow rate=1.0 mL/min): tR=13.8 min (4.4%), tR=18.3 min (95.6%);Mp: 128 C. (i-PrOH/hexane);IR (KBr): 3067, 1728, 1600, 1509, 776, 699 cm-1;1H NMR (CDCl3): delta8.29(s, 1H, 1'-H), 7.99-7.94 (m, 1H, Ph), 7.84-7.79 (m, 1H, Ph), 7.74 (t, J=7.0 Hz, 2H, Ph), 7.68 (d, J=8.0 Hz, 1H, Ph), 7.63 (d, J=8.5 Hz, 1H, Ph), 7.45-7.38 (m, 2H, Ph), 7.35-7.31 (m, 1H, Ph), 7.23-7.14 (m, 7H, Ph), 7.11 (t, J=7.5 Hz, 1H, Ph), 7.06 (d, J=7.5 Hz, 1H, Ph), 6.90 (d, J=7.0 Hz, 1H, Ph), 3.77 (q, J=7.0 Hz, 1H, 2-H), 1.45 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): delta173.5, 140.0, 134.8, 134.6, 133.8, 133.7, 131.2, 130.8, 129.1, 128.9, 128.7, 128.64, 128.57, 127.8, 127.2, 126.7, 126.4, 126.3, 125.9, 125.6, 125.2, 125.0, 123.5, 123.3, 71.1, 45.6, 18.2;HR MS: calculated for C30H24O2Na (M+Na+)=439.1669; found 439.1668.(S)-2-phenylpropionic acidHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/50/0.05 flow rate=0.5 mL/min): tR=39.6 min (24.1%), tR=43.4 min (75.9%);1H NMR (CDCl3): delta10.95 (br s, 1H, COOH), 7.30-7.16 (m, 5H, Ph), 3.67 (q, J=7.2 Hz, 1H, 2-H), 1.45 (d, J=7.2 Hz, 3H, 3-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 6-7

8
[ 15687-27-1 ]
[ 62784-66-1 ]
[ 1116086-46-4 ]
[ 51146-56-6 ]
[ 51146-57-7 ]

Yield	Reaction Conditions	Operation in experiment
39%	With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate;	Entry 44To a dichloromethane solution (1.0 mL) containing p-methoxybenzoic anhydride (68.9 mg, 0.241 mmol) and racemic ibuprofen (41.2 mg, 0.200 mmol); diisopropylethylamine (62.7 muL, 0.360 mmol), benzotetramisole (2.5 mg, 0.010 mmol), and 1,1-di(1-naphthyl)methanol (28.4 mg, 0.100 mmol) were added in order at room temperature. After stirring the reaction mixture solution at room temperature for 12 hr, the reaction was stopped with saturated ammonium chloride water. After fractionating the organic layer, the aqueous layer was extracted 4 times with diethylether. After combining the organic layers, they were dried with anhydrous sodium sulfate. After filtering the solution, it was vacuum concentrated, and the obtained mixture was fractionated by thin layer silica gel chromatography to obtain the corresponding optically active ibuprofen ester (36.9 mg, 39percent, 92percent ee) and the unreacted optically active ibuprofen (13.6 mg, 33percent, 36percent ee).(R)-ibuprofen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/ml): tR=6.1 min (4.1percent), tR=10.7 min (95.9percent);IR (neat): 3036, 1735, 1599, 1512, 782, 679 cm-1;1H NMR (CDCl3): delta8.29 (s, 1H, 1-H), 8.02-7.93 (m, 1H, Ph), 7.85-7.60 (m, 5H, Ph), 7.47-7.26 (m, 3H, Ph), 7.24-7.02 (m, 6H, Ph), 7.00-6.88 (m, 3H, Ph), 3.74 (q, J=7.1 Hz, 1H, 2-H), 2.38 (d, J=7.1 Hz, 2H, 1'-H), 1.78 (qq, J=6.6, 6.6 Hz, 1H, 2'-H), 1.43 (d, J=7.1 Hz, 3H, 3-H), 0.84 (d, J=6.6 Hz, 6H, 3'-H);13C NMR (CDCl3): delta173.7, 140.6, 137.2, 134.9, 134.7, 133.8, 133.7, 131.2, 130.9, 129.3, 129.1, 128.8, 128.7, 128.6, 127.5, 126.7, 126.3, 125.8, 125.6, 125.2, 125.0, 123.5, 123.4, 70.9, 45.3, 45.0, 30.2, 22.4, 18.1;HR MS: calculated for C34H32O2Na (M+Na+)=495.2295; found 495.2276.(S)-ibuprofenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/100/0.1, flow rate=1.0 mL/min); tR=26.3 min (77.5percent), tR=28.5 min (22.5percent);1H NMR (CDCl3): delta10.30 (br s, 1H, COOH), 7.14 (d, J=7.9 Hz, 2H, Ph), 7.02 (d, J=7.9 Hz, 2H, Ph), 3.63 (q, J=7.3 Hz, 1H, 2-H), 2.37 (q, J=7.3 Hz, 2H, 1'-H), 1.77 (qq, J=6.5, 6.5 Hz, 1H, 2'-H), 1.42 (d, J=7.3 Hz, 2H, 3-H), 0.82 (d, J=6.5 Hz, 6H, 3'-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 11-12

9
[ 942-54-1 ]
[ 62784-66-1 ]
[ 1116086-44-2 ]
di(1-naphthyl)methyl (S)-2-(4-methoxyphenyl)propanoate [ No CAS ]
[ 4842-49-3 ]
[ 24470-14-2 ]

Yield	Reaction Conditions	Operation in experiment
	With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate;Product distribution / selectivity;	Experimental Example 3Production of Optically Active Ester and Optically Active Carboxylic Acid Using 1,1-di(1-naphthyl)methanol As shown in the above reaction equation, an optically active ester and optically active carboxylic acid were obtained by reacting 1,1-di(1-naphthyl)methanol and various racemic carboxylic acids. The results are shown in Table 3.; Entry 20di(1-naphthyl)methyl (R)-2-(4-methoxyphenyl)propanoateHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/min); tR=10.5 min (7.2%), tR=12.8 min (85.6%);IR (neat): 3059, 1733, 1608, 1512, 783, 733 cm-1;1H NMR (CDCl3): delta8.26 (s, 1H, 1'-H), 7.97-7.89 (m, 1H, Ph), 7.85-7.58 (m, 5H, Ph), 7.46-7.04 (m, 8H, Ph), 6.93 (d, J=6.9 Hz, 1H, Ph), 6.75-6.67 (m, 2H, Ph), 3.78-3.68 (m, 4H, 2-H, OMe), 1.42 (d, J=6.9 Hz, 3H, 3-H);13C NMR (CDCl3): delta173.7, 158.7, 134.8, 134.6, 133.8, 133.6, 132.1, 131.2, 130.9, 129.1, 128.83, 128.76, 128.7, 128.6, 128.3, 126.7, 126.3, 126.2, 125.8, 125.6, 125.3, 125.2, 125.0, 123.5, 123.3, 113.9, 71.0, 55.3, 44.8, 18.2;HR MS: calculated for C31H26O2Na (M+Na+)=469.1774; found 469.1754.(S)-2-(4-methoxyphenyl)propionic acidHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/50/0.05, flow rate=1.0 mL/min); tR=34.7 min (17.5%), tR=36.4 min (82.5%);1H NMR (CDCl3): delta10.99 (br s, 1H, COOH), 7.17 (d, J=8.7 Hz, 2H, Ph), 6.79 (d, J=8.7 Hz, 2H, Ph), 3.72 (s, 3H, OMe), 3.61 (q, J=7.2 Hz, 1H, 2-H), 1.42 (d, J=7.2 Hz, 3H, 3-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641
[3]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 6

10
[ 23981-80-8 ]
[ 62784-66-1 ]
(R)-naproxen di(1-naphthyl)methyl ester [ No CAS ]
[ 1116086-50-0 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Yield	Reaction Conditions	Operation in experiment
	With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate;Product distribution / selectivity;	Experimental Example 8Production of Optically Active Ester and Optically Active Carboxylic Acid Using Naproxen (Optical Resolution of Naproxen) As shown by the above reaction equation, an optically active ester and optically active carboxylic acid are obtained by reacting 1,1-di(1-naphthyl)methanol or 1,1-di(9-phenanthryl)methanol and racemic naproxen. The results are shown in Table 8.; Entry 53(R)-naproxen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=1.0 mL/ml): tR=13.7 min (10.6%), tR=17.4 min (89.4%);IR (neat): 3034, 1733, 1604, 1508, 782, 679 cm-1;1H NMR (CDCl3): delta8.29 (s, 1H, 1'-H), 8.00-7.90 (m, 1H, Ph), 7.82-6.96 (m, 17H, Ph), 6.95-6.81 (m, 2H, Ph), 3.86 (q, J=7.0 Hz, 1H, 2-H), 3.79 (s, 3H, OMe), 1.49 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): delta173.6, 157.6, 135.1, 134.7, 134.5, 133.8, 133.7, 133.6, 131.2, 130.8, 129.3, 129.1, 128.9, 128.8, 128.7, 128.6, 128.3, 127.1, 126.7, 126.5, 126.3, 126.2, 125.8, 125.6, 125.3, 125.2, 125.0, 123.4, 123.3, 118.9, 105.5, 71.2, 55.2, 45.5, 18.3;HR MS: calculated for C35H28O3Na (M+Na+)=519.1931; found 519.1932.

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641
[3]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641
[4]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 13-14

11
[ 23981-80-8 ]
[ 62784-66-1 ]
[ 1116086-50-0 ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641

12
[ 29679-58-1 ]
[ 62784-66-1 ]
[ 1116086-48-6 ]
(S)-fenoprofen di(1-naphthyl)methyl ester [ No CAS ]
[ 33028-97-6 ]
(R)-fenoprofen [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate;Product distribution / selectivity;	Entry 60To a dichloromethane solution (1.0 mL) containing p-methoxybenzoic anhydride (68.7 mg, 0.240 mmol) and racemic fenoprofen (48.2 mg, 0.199 mmol), and 1,1-di(naphthyl)methanol (28.2 mg, 0.099 mmol); diisopropylethylamine (62.7 muL, 0.360 mmol) and benzotetramisole (2.5 mg, 0.010 mmol), were added in order at room temperature. After stirring the reaction mixture solution at room temperature for 12 hr, the reaction was stopped with saturated ammonium chloride water. After fractionating the organic layer, the aqueous layer was extracted 4 times with diethyl ether. After combining the organic layers, they were dried with anhydrous sodium sulfate. After filtering the solution, it was vacuum concentrated, and the obtained mixture was fractionated by thin layer silica gel chromatography to obtain the corresponding optically active fenoprofen ester (46.8 mg, 46%, 82% ee) and the unreacted optically active fenoprofen (20.2 mg, 42%, 53% ee).(R)-fenoprofen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/50, flow rate=1.0 mL/ml): tR=20.4 min (8.9%), tR=23.9 min (91.1%);IR (neat): 3036, 1735, 1585, 1484, 781, 679 cm-1;1H NMR (CDCl3): delta8.28 (s, 1H, 1'-H), 7.92 (d, J=8.0 Hz, 1H, Ph), 7.82-7.62 (m, 5H, Ph), 7.43-7.30 (m, 3H, Ph), 7.27-7.09 (m, 7H, Ph), 6.98-6.91 (m, 3H, Ph), 6.86-6.83 (m, 1H, Ph), 6.82-6.73 (m, 3H, Ph), 3.72 (q, J=7.0 Hz, 1H, 2-H), 1.42 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): delta173.1, 157.3, 157.0, 141.9, 134.7, 134.6, 133.8, 133.7, 131.2, 130.9, 129.8, 129.7, 129.1, 128.9, 128.8, 128.7, 128.3, 126.7, 126.4, 126.1, 125.9, 125.7, 125.3, 125.2, 125.1, 123.4, 123.3, 123.1, 122.6, 118.7, 118.4, 117.6, 71.2, 45.5, 17.9;HR MS: calculated for C36H28O3Na (M+Na+)=531.1931; found 531.1948.(S)-fenoprofenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/50/0.05, flow rate=1.0 mL/min); tR=26.0 min (23.4%), tR=30.9 min (76.6%);1H NMR (CDCl3): delta11.8 (br s, 1H, COOH), 7.24-7.10 (m, 3H, Ph), 7.00-6.85 (m, 5H, Ph), 6.76 (ddd, J=8.2, 2.5, 0.9 Hz, 1H, Ph), 3.58 (q, J=7.2 Hz, 1H, 2-H), 1.37 (d, J=7.2 Hz, 3H, 3-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641
[3]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 15-16

13
[ 22071-15-4 ]
[ 62784-66-1 ]
[ 1116086-47-5 ]
(S)-ketoprofen di(1-naphthyl)methyl ester [ No CAS ]
[ 22161-81-5 ]
[ 56105-81-8 ]

Yield	Reaction Conditions	Operation in experiment
	With benzoic acid anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 6h;Resolution of racemate;Product distribution / selectivity;	Entry 49To a dichloromethane solution (2.0 mL) containing benzoic anhydride (54.2 mg, 0.240 mmol) and racemic ketoprofen (50.8 mg, 0.200 mmol); diisopropylethylamine (62.7 muL, 0.360 mmol), benzotetramisole (2.5 mg, 0.010 mmol), and 1,1-di(1-naphthyl)methanol (28.4 mg, 0.100 mmol) were added in order at room temperature. After stirring the reaction mixture solution at room temperature for 6 hr, the reaction was stopped with saturated ammonium chloride water. After fractionating the organic layer, the aqueous layer was extracted 4 times with diethylether. After combining the organic layers, they were dried with anhydrous sodium sulfate. After filtering the solution, it was vacuum concentrated, and the obtained mixture was fractionated by thin layer silica gel chromatography to obtain the corresponding optically active ketoprofen ester (56.8 mg, 55%, 80% ee) and the unreacted optically active ketoprofen (13.8 mg, 27%, 50% ee).(R)-ketoprofen di(1-naphthyl)methylesterHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/4, flow rate=1.0 mL/ml): tR=16.7 min (10.1%), tR=46.3 min (89.9%);IR (neat): 3035, 1735, 1660, 1599, 1511, 780, 680 cm-1;1H NMR (CDCl3): delta8.28 (s, 1H, 1'-H), 7.93-7.85 (m, 1H, Ph), 7.82-7.54 (m, 6H, Ph), 7.52-7.44 (m, 2H, Ph), 7.44-7.06 (m, 13H, Ph), 6.95 (d, J=7.1 Hz, 1H, Ph), 3.81 (q, J=7.1 Hz, 1H, 2-H), 1.46 (d, J=7.1 Hz, 3H, 3-H);13C NMR (CDCl3): delta196.3, 173.0, 140.1, 137.8, 137.3, 134.5, 134.4, 133.8, 133.7, 132.4, 131.6, 131.1, 130.8, 129.9, 129.5, 129.2, 128.93, 128.91, 128.86, 128.7, 128.6, 128.3, 128.2, 126.7, 126.4, 126.1, 125.9, 125.7, 125.4, 125.2, 125.0, 123.2, 71.4, 45.5, 17.9.HR MS: calculated for C37H28O3Na (M+Na+)=543.1931; found 543.1910.(S)-ketoprofenHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/10/0.01, flow rate=1.0 mL/min); tR=15.0 min (20.0%), tR=17.7 min (80%);1H NMR (CDCl3): delta10.67 (br s, 1H, COOH), 7.85-7.76 (m, 3H, Ph), 7.69 (dt, J=7.5, 1.5 Hz, 1H, Ph), 7.63-7.54 (m, 2H, Ph), 7.52-7.42 (m, 3H, Ph), 3.83 (q, J=7.0 Hz, 1H, 2-H), 1.56 (d, J=7.0 Hz, 3H, 3-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641
[3]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 12-13

14
[ 938-94-3 ]
[ 62784-66-1 ]
[ 1116086-43-1 ]
di(1-naphthyl)methyl (S)-2-(4-methylphenyl)propanoate [ No CAS ]
[ 124709-71-3 ]
[ 124709-72-4 ]

Yield	Reaction Conditions	Operation in experiment
	With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate;Product distribution / selectivity;	Experimental Example 3Production of Optically Active Ester and Optically Active Carboxylic Acid Using 1,1-di(1-naphthyl)methanol As shown in the above reaction equation, an optically active ester and optically active carboxylic acid were obtained by reacting 1,1-di(1-naphthyl)methanol and various racemic carboxylic acids. The results are shown in Table 3.; Entry 18di-(1-naphthyl)methyl (R)-2-(4-tolyl)propanoateHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=0.75 mL/min): tR=9.5 min (7.6%), tR=13.4 min (92.4%);IR (neat): 3051, 1733, 1598, 1512, 801, 777, 732 cm-1;1H NMR (CDCl3): delta8.27 (s, 1H, 1'-H), 7.98-7.91 (m, 1H, Ph), 7.83-7.76 (m, 1H, Ph), 7.72 (t, J=8.2 Hz, 2H, Ph), 7.66 (d, J=8.2 Hz, 1H, Ph), 7.62 (d, J=8.6 Hz, 1H, Ph), 7.44-7.36 (m, 1H, Ph), 7.31 (t, J=7.5 Hz, 1H, Ph), 7.22-7.14 (m, 2H, Ph), 7.13-7.01 (m, 4H, Ph), 6.97 (d, J=7.9 Hz, 2H, Ph), 6.92 (d, J=7.5 Hz, 1H, Ph), 3.72 (q, J=7.0, 1H, 2-H), 2.25 (s, 3H, Me), 1.42 (d, J=7.0, 3H, 3-H);13C NMR (CDCl3): delta173.7, 137.0, 136.7, 134.9, 134.6, 133.8, 133.7, 131.2, 130.9, 129.2, 129.1, 128.8, 128.7, 128.6, 128.3, 127.6, 126.7, 126.3, 126.2, 125.8, 125.6, 125.3, 125.2, 125.0, 123.5, 123.3, 71.1, 45.2, 21.0, 18.2;HR MS: calculated for C31H26O2 (M+Na+)=453.1825; found 453.1816.(S)-2-(4-tolyl)propionic acidHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/50/0.05, flow rate=0.5 mL/min); tR=43.2 min (23.0%), tR=46.7 min (77.0%);1H NMR (CDCl3): delta10.63 (br s, 1H, COOH), 7.13 (d, J=7.8, 2H, Ph), 7.07 (d, J=7.8, 2H, Ph), 3.63 (q, J=7.0 Hz, 1H, 2-H), 2.26 (s, 3H, Me), 1.42 (d, J=7.0 Hz, 3H, 3-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641
[3]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 6

15
[ 938-95-4 ]
[ 62784-66-1 ]
[ 1116086-45-3 ]
di(1-naphthyl)methyl (S)-2-(4-chlorophenyl)propanoate [ No CAS ]
[ 105879-63-8 ]
[ 105879-62-7 ]

Yield	Reaction Conditions	Operation in experiment
	With p-Methoxybenzoic anhydride; N-ethyl-N,N-diisopropylamine;(R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In dichloromethane; at 20℃; for 12h;Resolution of racemate;Product distribution / selectivity;	Experimental Example 3Production of Optically Active Ester and Optically Active Carboxylic Acid Using 1,1-di(1-naphthyl)methanol As shown in the above reaction equation, an optically active ester and optically active carboxylic acid were obtained by reacting 1,1-di(1-naphthyl)methanol and various racemic carboxylic acids. The results are shown in Table 3.; Entry 22di(1-naphthyl)methyl (R)-2-(4-chlorophenyl)propanoateHPLC (CHIRALPAK AD-H, i-PrOH/hexane=1/9, flow rate=0.5 mL/min); tR=17.1 min (8.4%), tR=19.3 min (91.6%);IR (neat): 3052, 1737, 1599, 1510, 837, 777 cm-1;1H NMR (CDCl3): delta8.26 (d, J=3.0 Hz, 1H, 1'-H), 7.90 (dd, J=7.5, 3.0 Hz, 1H, Ph), 7.81 (d, J=7.5 Hz, 1H, Ph), 7.75 (t, J=8.5 Hz, 2H, Ph), 7.70 (d, J=8.0 Hz, 1H, Ph), 7.62 (dd, J=8.5, 3.0 Hz, 1H, Ph), 7.45-7.32 (m, 3H, Ph), 7.26-7.04 (m, 8H, Ph), 6.93 (dd, J=7.0, 3.0 Hz, 1H, Ph), 3.73 (qd, J=8.5, 1.5 Hz, 1H, 2-H), 1.45-1.41 (m, 3H, 3-H);13C NMR (CDCl3): delta173.1, 138.4, 134.5, 134.4, 133.8, 133.7, 133.0, 131.1, 130.8, 129.2, 129.1, 128.9, 128.7, 128.6, 128.3, 126.7, 126.4, 126.1, 125.9, 125.7, 125.3, 125.2, 124.5, 123.3, 123.2, 71.4, 45.0, 18.0;HR MS: calculated for C30H23O2ClNa (M+Na+)=473.1279; found 473.1284.(S)-2-(4-chlorophenyl)propionic acidHPLC (CHIRALPAK AD-H, i-PrOH/hexane/TFA=1/50/0.05, flow rate=0.75 mL/min); tR=31.7 min (21.4%), tR=34.0 min (78.6%);1H NMR (CDCl3): delta9.15 (br s, 1H, COOH), 7.39-7.09 (m, 4H, Ph), 3.69 (q, J=7.0 Hz, 1H, 2-H), 1.48 (d, J=7.0 Hz, 3H, 3-H).

Reference： [1]European Journal of Organic Chemistry,2008,p. 5887 - 5890
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11629 - 11641
[3]Patent: US2010/234610,2010,A1 .Location in patent: Page/Page column 6

16
[ 58048-38-7 ]
[ 62784-66-1 ]
[ 1213744-25-2 ]
[ 120-36-5 ]
[ 15165-67-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304

17
[ 62784-66-1 ]
[ 446878-78-0 ]
[ 1213744-22-9 ]
[ 1129-46-0 ]
[ 1912-23-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304

18
[ 62784-66-1 ]
[ 52344-67-9 ]
(R)-naproxen di(1-naphthyl)methyl ester [ No CAS ]
[ 22204-53-1 ]
[ 23979-41-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304

19
[ 62784-66-1 ]
2-(4-isobutylphenyl)propionic anhydride [ No CAS ]
[ 1116086-46-4 ]
[ 51146-56-6 ]
[ 51146-57-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2301 - 2304

20
4-(2-methylsulfanyl-ethyl)-2-phenyl-4<i>H</i>-oxazol-5-one [ No CAS ]
[ 62784-66-1 ]
[ 1208867-91-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With S-BTM; sodium sulfate; benzoic acid In chloroform-d1 at 20℃; for 72h; optical yield given as %ee; enantioselective reaction;