Name: Hydroxyacetone
Brand: Ambeed
SKU: A244029
Rating: 4.8 (95 reviews)

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Hydroxyacetone is an endogenous metabolic product in humans, typically used as an intermediate in organic synthesis.

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Quality Control of Hydroxyacetone Purity: 97% contains ≤500 ppm sodium carbonate as stabilizer SDS Specification

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Product Details of Hydroxyacetone

CAS No. :	116-09-6
Formula :	C₃H₆O₂
M.W :	74.08
SMILES Code :	CC(CO)=O
English Name :	Hydroxyacetone
MDL No. :	MFCD00004669
InChI Key :	XLSMFKSTNGKWQX-UHFFFAOYSA-N
Pubchem ID :	8299

Safety of Hydroxyacetone

GHS Pictogram:
Signal Word:
Hazard Statements:
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Class:
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Packing Group:

Application In Synthesis of Hydroxyacetone

* 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.

Downstream synthetic route of [ 116-09-6 ]

[ 116-09-6 ] Synthesis Path-Downstream 1~66

1
[ 186581-53-3 ]
[ 116-09-6 ]
[ 5077-67-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1930,vol. 484,p. 17.

2
[ 6168-72-5 ]
[ 116-09-6 ]
[ 2294-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; platinum Hydrogenation;
	With hydrogen In methanol Ambient temperature;
	In methanol	9 2-[(2-Hydroxy-1-methylethyl)amino]-1-propanol STR54 Preparation 9 2-[(2-Hydroxy-1-methylethyl)amino]-1-propanol STR54 Platinum dioxide (40 mg) was added to a solution of dl-2-amino-1-propanol (6.4 ml) and hydroxyacetone (7.0 g) in methanol (75 ml) over 3 A molecular sieves. The reaction mixture was hydrogenated at 60 psi. for 18 hours, after which time the catalyst was filtered off and the solvent removed under reduced pressure. The crude product was purified by distillation, b.pt. 94° C.ã0.2 mbar to afford 2-[(2-hydroxy-1-methylethyl)amino]-1-propanol (3.66 g) as a yellow oil. 1 H-NMR (CDCl3)δ: 3.60 (2H, m), 3.30 (2H, m), 2.90 (2H, m), 2.40 (3H, bs), 1.10 (3H, d), 1.05 (3H, d).

	With platinum(IV) oxide; hydrogen In ethanol at 20℃; for 24h;	13 Synthesis of 2,2'-azanediyldipropan-l-ol Synthesis of 2,2'-azanediyldipropan-l-ol: O NH, HO HO HO OH Pt02/H2 EtOH [00288] 2-Aminopropan-l -ol (5 g, 66.57 mmol) and l-hydroxypropan-2-one (5.77g, 77.89 mmol) were dissolved in ethanol (115 mL) and 50 mg of Pt02 was added. The reaction mixture was stirred at 50 psi H2 pressure at room temperature for 24 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give the crude product, which was used without further purification in the following step. Crude yield: 79 %. 1H NMR (400 MHz, CDC13) δ 4.45 (bs, 2H), 3.42-3.43 (m, 1H), 3.16-3.22 (m, 4H), 2.65-2.69 (m, 2H) 0.87-0.91(m, 6H): LCMS m/z 133.99 [M+H]+ , tR: 4.077 min .
	With platinum(IV) oxide; hydrogen In methanol for 20h;	28.1 Step 1 : Platinum dioxide (800 mg) was added to a solution of

References: [1]Berlin; Sytschewa [Zhurnal Obshchei Khimii, 1950, vol. 20, p. 577,579;engl.Ausg.S.609,611].
[2]Maillard,J. et al. [Chimica Therapeutica, 1969, vol. 4, p. 80 - 88].
[3]Current Patent Assignee: PFIZER - US6166011, 2000, A.
[4]Current Patent Assignee: KARYOPHARM THERAPEUTICS - WO2013/170068, 2013, A2 Location in patent: Paragraph 00288.
[5]Current Patent Assignee: MERCK SHARP DOHME - WO2014/48065, 2014, A1 Location in patent: Page/Page column 92-93.

3
[ 420-04-2 ]
[ 116-09-6 ]
[ 35629-70-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	In water at 45℃; for 0.5h;
	In water
	With sodium hydroxide

	With ammonium hydroxide In methanol; water
	With sodium hydroxide In tetrahydrofuran
35 g	In water at 50 - 60℃; for 0.166667h;
	With sodium hydroxide In water	19 2-Amino-4-methyloxazole EXAMPLE 19 2-Amino-4-methyloxazole 5N Sodium hydroxide solution (125 ml.) was added dropwise to a stirred solution of hydroxyacetone (74 g., 1 mol) and cyanamide (42 g., 1 mol) in water (110 ml.). The mixture rapidly became hot and was cooled to 20° C and stirred at this temperature for 1 hour and then extracted with ether (3 * 250 ml.). The ether extract was washed with sodium chloride solution, dried over sodium sulphate and then evaporated under vacuum. The residue was distilled under vacuum to give the product 76.8 g. (78%) b.p. 66°-67° C/0.5 mm. nd23 1.495.

References: [1]Ohta, Hiroshi; Ishizaka, Tomoko; Tatsuzuki, Makoto; Yoshinaga, Mitsukane; Iida, Izumi; Yamaguchi, Tomomi; Tomishima, Yasumitsu; Futaki, Nobuko; Toda, Yoshihisa; Saito, Shuji [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1111 - 1124].
[2]Crank; Foulis [Journal of medicinal chemistry, 1971, vol. 14, # 11, p. 1075 - 1077].
[3]Ross; Harrison; Jolley; Neville; Todd; Verge; Dawson; Sweatman [Journal of Medicinal Chemistry, 1979, vol. 22, # 4, p. 412 - 417].
[4]Rapi; Ginanneschi; Chelli [Journal of the Chemical Society. Perkin transactions I, 1975, # 19, p. 1999 - 2001].
[5]Cockerill,A.F. et al. [Synthesis, 1976, p. 591 - 593].
[6]Crank, George; Khan, Humaid R. [Australian Journal of Chemistry, 1985, vol. 38, # 3, p. 447 - 458].
[7]Current Patent Assignee: LILLY INDUSTRIES - US4122183, 1978, A.

4
[ 69-65-8 ]
[ 110-00-9 ]
[ 75-07-0 ]
[ 141-46-8 ]
[ 5077-67-8 ]
[ 116-09-6 ]
[ 431-03-8 ]

References: [1]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 1624 - 1626.

5
[ 50-70-4 ]
[ 110-00-9 ]
[ 75-07-0 ]
[ 141-46-8 ]
[ 5077-67-8 ]
[ 116-09-6 ]
[ 431-03-8 ]

References: [1]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 1624 - 1626.

6
[ 87-99-0 ]
[ 110-00-9 ]
[ 600-14-6 ]
[ 75-07-0 ]
[ 141-46-8 ]
[ 5077-67-8 ]
[ 116-09-6 ]

References: [1]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 1624 - 1626.

7
[ 18162-48-6 ]
[ 116-09-6 ]
[ 74685-00-0 ]

Yield	Reaction Conditions	Operation in experiment
98.3%	Stage #1: Hydroxyacetone With 1H-imidazole In dichloromethane at 0 - 5℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride at 0 - 35℃; for 6h; Inert atmosphere;	1 Embodiment 1 Under nitrogen protection, 1-hydroxypropyl-2-ketone (100 g, 1.0 eq) was added to 500 mL of dichloromethane, and imidazole (229.8 g, 2.5 eq) was added to the reaction solution, and the internal temperature was controlled at 0-5°C and stirred for 30 min. The reaction solution was clear and transparent, and TBDMSCl (244.2 g, 1.2 eq) was then added in batches, and the internal temperature of the reaction solution was controlled at 0-5°C. After the addition was completed, the temperature was raised to 25-35°C and stirred for 3 h. Thin layer chromatography (TLC) was used. The reaction was followed and the reaction was completed after 3 hours. The dichloromethane was removed by concentration under reduced pressure to obtain a colorless oily liquid. Methyl tert-butyl ether (500 mL) and water (200 mL) were then added to the oily liquid, and the mixture was stirred at 25°C for 30 minutes. The mixture was allowed to stand for separation and the organic phase was retained. The organic phase was then washed once with water (100 mL), allowed to stand for separation, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure at 40°C to obtain the compound of formula 2A (250 g, yield 98.3%) as a colorless oily liquid.
95%	With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere;
94%	With 1H-imidazole In N,N-dimethyl-formamide

92.43%	With 1H-imidazole In dichloromethane at 0 - 20℃; for 12h;	6 To a solution of l-hydroxypropan-2-one (20 g, 269.98 mmol, 18.52 mL, 1 eq.) and imidazole (25.73 g, 377.98 mmol, 1.4 eq.) in DCM (200 mL) was added TB SCI (44.76 g, 296.98 mmol, 36.39 mL, 1.1 eq.) at 0 °C. The mixture was stirred at 20 °C for 12 h. The mixture was concentrated under reduced pressure to give a residue. The residue was diluted with H2O (200 mL), extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SC>4, filtered and concentrated under reduced pressure to give the crude 7(2) (47 g, 249.55 mmol, 92.43% yield) as a yellow oil, which was used into the next step without further purification
88%	With 1H-imidazole In dichloromethane at 0℃; for 5h; Inert atmosphere; Schlenk technique;	1-((tert-Butyldimethylsilyl)oxy)propan-2-one (26) tert-Butyldimethylsilyl chloride (2.48 g, 16.5 mmol, 1.1 equiv) was added to a stirred solution of 1-hydroxypropan-2-one (25, 1.11 g, 15.0 mmol, 1.0 equiv) and imidazole (1.43 g, 21.0 mmol, 1.4 equiv) in20 mL dry dichloromethane at 0 °C. The mixture was stirred for 5 h at the same temperature, the solventwas evaporated under reduced pressure and the residue was extracted three times with diethyl ether andfinally washed with water. The combined organic layer was dried over MgSO4, filtered, concentrated andpurified by column chromatography on silica gel (50 g) with ethyl acetate/hexane 1:40 as the eluent, whichyielded the desired TBS-protected ketone as colorless liquid (2.48 g, 13.2 mmol, 88%). Rf: 0.18(ethyl acetate/hexane = 1:40); 1H-NMR (500.13 MHz, CDCl3): δ = 0.09 (s, 6H), 0.93 (s, 9H), 2.17 (s, 3H),4.15 (s, 2H); 13C-NMR (125.77 MHz, CDCl3): δ = -5.5, 18.3, 25.7, 69.6, 209.2; HR-MS (EI+): calculated forC9H20O2Si+ [M]+: m/z = 188.1227, found: m/z = 188.1242.
88%	With 1H-imidazole In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique;
88%	With 1H-imidazole In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
83%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;
78%	With 1H-imidazole In N,N-dimethyl-formamide for 21h; Ambient temperature;
78%	With 1H-imidazole In dichloromethane at 0℃; for 5h;
78.7%	With 1H-imidazole In dichloromethane at 0 - 20℃; for 13h;	11.1 Step 1: Preparation of 1-((tert-butyldimethylsilyl)oxy)propan-2-one (11b) Hydroxyacetone 11a (100 g, 1.35 mol) was dissolved in dichloromethane (1 L) at room temperature.The solution was cooled to 0°C, and imidazole (175 g, 2.57 mol) and tert-butyldimethylsilyl chloride (245 g, 1.63 mol) were added sequentially.The reaction solution was stirred at 0°C for 1 hour, then slowly warmed to room temperature, and stirring was continued for 12 hours.After the reaction was completed, the reaction solution was washed with water (3×1 L), and the organic phase was concentrated under reduced pressure to obtain compound 11b (200 g, 78.7%) as a pale yellow liquid.
78%	With dmap; triethylamine In dichloromethane at 20℃; for 7h;	1.1-3.1 S1: Dissolve 5g of hydroxyacetone in 60mL of dichloromethane, then add 12g of tert-butyldimethylsilyl chloride and 10.7g of 4-dimethylaminopyridine, and then add 9g of triethylamine, stir at room temperature for 7h, after the reaction is complete, add 60mL of ether, wash the organic phase with 50mL of saturated brine, dry with 4g of anhydrous sodium sulfate, and concentrate the organic phase to obtain a colorless oil (Compound I), with a yield of 78%.
75%	With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere of nitrogen;	96 To a DCM (5 mL) solution of l-hydroxypropan-2-one (500 mg, 6.8 mmol), DMAP (41 mg, 0.34 mmol) and Et3N (1.2 mL, 8.16 mmol) was added TBSCl (1.133 g, 7.5 mmol) at O0C under nitrogen atmosphere. The mixture was stirred at r.t. for 2h. Then the mixture was added water and extracted with EtOAc. The organic layer was purified by silica gel chromatography using PE/EA (10/1) to give the title compound (950 mg, 75%). EDI-MS (M+l): 189. 1H NMR (300 MHz, CDCl3) δ 4.057 (s, 2H), 2.080 (s, 3H), 0.832 (s, 9H), 0.001 (s, 6H).
73%	With 1H-imidazole In N,N-dimethyl-formamide
72%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 24h; Ambient temperature;
70%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 2h;
62%	With 1H-imidazole; dmap In dichloromethane at 0℃; for 1h;
54%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	A35 Preparation of intermediate 173 1-Hydroxy-2-propanone (3 g, 36.5 mmol) was dissolved in DCM (30 ml) and cooledunder nitrogen to 0°CTriethylamine (6.8 mL, 48.6 mmol) and DMAP (0.25 g,2.02 mmol) were added at 0°C. Tert-Butyldimethylsilyl chloride (6.8 mL, 45 mmol) was added in one portion and the reaction was stirred for 2 hours at room temperature. The reaction was quenched by addition of water (40 ml). The aqueous layer wasextracted with DCM (3 x 25 ml) and the combined organic layers were dried oversodium sulphate, filtered and evaporated in vacuo to give a brown oil. The crude material was purified by silica gel chromatography (50g) eluting with cyclohexanefollowed by 5% EtOAc/cyclohexane to give 3.7 g (54% yield) of intermediate 173 as a clear oil.
	With dmap; triethylamine In dichloromethane at 20℃; for 12h;
35 g	With 1H-imidazole In N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere;	1 In a 500 mL round bottom flask, a solution of l-hydroxy-2- propanone (24.3g, 0.32 mol, Sigma-Aldrich, India) in DMF (225 mL) maintained at rt, was treated with TBDMS-chloride (37. lg, 0.229 mol, Sigma-Aldrich, India), and imidazole (40.19g, 0.591 mol, Sigma-Aldrich, India). The solution was heated to 40°C for 2 hours under nitrogen atmosphere. Upon completion of reaction (TLC, 10% EtOAc-hexane, R 0.6), the reaction mixture was diluted with cold water (300 mL) and extracted with hexanes (250 mL x 4). The combined organic extract was washed with brine and concentrated under reduced pressure to give l-((tert-butyl(dimethyl)silyl)oxy)-2-propanone (35 g) as a colorless liquid.
	With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Glovebox; Schlenk technique; Inert atmosphere; Cooling with ice;
78.7 %	With 1H-imidazole In dichloromethane at 0 - 20℃;	1.1 Step 1: Preparation of 1-((tert-butyldimethylsilyl)oxy)propan-2-one (1b) Hydroxyacetone 1a (100 g, 1.35 mol) was dissolved in dichloromethane (DCM) (1 L) at room temperature.The solution was cooled to 0° C., and imidazole (175 g, 2.57 mol) and tert-butyldimethylsilyl chloride (TBDMSCl) (245 g, 1.63 mol) were sequentially added.The reaction solution was stirred at 0°C for 1 hour, then slowly warmed to room temperature, and stirring was continued for 12 hours.After the reaction was complete, the reaction solution was washed with water (3×1 L), and the organic phase was concentrated under reduced pressure to obtain light yellow liquid compound 1b (200 g, 78.7%).

References: [1]Current Patent Assignee: HEZE HAOYUAN PHARMACEUTICAL TECH - CN119504830, 2025, A Location in patent: Paragraph 0098-0101.
[2]Davey, Martin S.; Malde, Roshni; Mykura, Rory C.; Baker, Alfie T.; Taher, Taher E.; Le Duff, Cécile S.; Willcox, Benjamin E.; Mehellou, Youcef [Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 2111 - 2117].
[3]Baldwin, Ian R.; Whitby, Richard J. [Chemical Communications, 2003, # 22, p. 2786 - 2787].
[4]Current Patent Assignee: ALIGOS THERAPEUTICS INC - WO2020/167984, 2020, A1 Location in patent: Paragraph 0186.
[5]Bretzke, Sebastian; Scheeff, Stephan; Vollmeyer, Felicitas; Eberhagen, Friederike; Rominger, Frank; Menche, Dirk [Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1111 - 1121].
[6]Peil, Sebastian; Guthertz, Alexandre; Biberger, Tobias; Fürstner, Alois [Angewandte Chemie - International Edition, 2019, vol. 58, # 26, p. 8851 - 8856][Angew. Chem., 2019, vol. 131, # 26, p. 8943 - 8948,6].
[7]Peil, Sebastian; Bistoni, Giovanni; Goddard, Richard; Fürstner, Alois [Journal of the American Chemical Society, 2020, vol. 142, # 43, p. 18541 - 18553].
[8]Eisenfuehr, Alexander; Arora, Paramjit S; Sengle, Gerhard; Takaoka, Leo R; Nowick, James S; Famulok, Michael [Bioorganic and medicinal chemistry, 2003, vol. 11, # 2, p. 235 - 249].
[9]Kozikowski, Alan P.; Okita, Makoto; Kobayashi, Motomasa; Floss, Heinz G. [Journal of Organic Chemistry, 1988, vol. 53, # 4, p. 863 - 869].
[10]Wu, Ying; Hong, Joon Hee [Archiv der Pharmazie, 2005, vol. 338, # 11, p. 517 - 521].
[11]Current Patent Assignee: CHINA MEDICINE RESEARCH AND DEVELOPMENT CENTER - WO2022/17408, 2022, A1 Location in patent: Page/Page column 59.
[12]Current Patent Assignee: XIAN RUIPUYUAN BIOTECHNOLOGY - CN119552105, 2025, A Location in patent: Paragraph 0041-0043; 0044; 0053.
[13]Current Patent Assignee: BIOGEN MA - WO2010/51031, 2010, A1 Location in patent: Page/Page column 62.
[14]Jew, Sang-Sup; Kim, Hyun-Ah; Song, Sam-Mi; Jang, Jung-Sook; Park, Hyeung-Geun [Heterocycles, 1998, vol. 47, # 1, p. 153 - 156].
[15]Chaouni-Benabdallah, Aziz; Subra, Guy; Bonnet, Pierre A.; Fernandez, Jean P.; Chapat, Jean P.; Vallet, Patrick; Muller, Robert N. [Tetrahedron, 1994, vol. 50, # 45, p. 12923 - 12932].
[16]Choo, Hea-Young Park; Peak, Kyung-Hee; Park, Jongsei; Kim, Dong Hyun; Chung, Hak Soon [European Journal of Medicinal Chemistry, 2000, vol. 35, # 6, p. 643 - 648].
[17]Huang, He; Forsyth, Craig J. [Journal of Organic Chemistry, 1997, vol. 62, # 24, p. 8595 - 8596].
[18]Current Patent Assignee: JANSSEN CILAG - WO2019/8011, 2019, A1 Location in patent: Page/Page column 160.
[19]Martinez, M. Montserrat; Hoppe, Dieter [European Journal of Organic Chemistry, 2005, # 7, p. 1427 - 1443].
[20]Current Patent Assignee: AMGEN - WO2013/173382, 2013, A1 Location in patent: Page/Page column 233.
[21]Mannisto, Jere K.; Sahari, Aleksi; Lagerblom, Kalle; Niemi, Teemu; Nieger, Martin; Sztanó, Gábor; Repo, Timo [Chemistry - A European Journal, 2019, vol. 25, # 44, p. 10284 - 10289].
[22]Current Patent Assignee: CHINA MEDICINE RESEARCH AND DEVELOPMENT CENTER - WO2023/78241, 2023, A1 Location in patent: Page/Page column 36; 37.

8
[ 2749-11-3 ]
[ 116-09-6 ]
[ 154596-17-5 ]
[ 154634-94-3 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

References: [1]Enders; Meyer; Raabe; Runsink [Synthesis, 1994, # 1, p. 66 - 72].

9
[ 116-09-6 ]
[ 109-77-3 ]
[ 5117-87-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With triethylamine; In methanol; at 0 - 20℃;	To a mixture of malonontrile (0.96 g, 14.6 mmol), acetol (1.08 g, 14.6 mmol) in methanol (10 mL) at 0 C. was added, dropwise, triethylamine (2.0 mL). The reaction mixture was stirred at room temperature overnight. After removal of solvent under reduced pressure the crude solid was washed with cold isopropanol to give product as white powder (0.54 g, 30%). HPLC/MS: (M+H)+ 123.3 m/z. Retention time (LC-MS)=1.81 min. 1H NMR (CD3OD): 6.58(s, 1H,); 1.95 (s, 3H).
	With triethylamine; In methanol; at 20℃;	To a solution of hydroxyacetone (1.0 g, 13.5 mmol) in 45 mL MeOH was added a solution of malonitrile (0.9 g, 13.5 mmol) in TEA (1.36 g, 13.5 mmol) and 10 mL MeOH. After stirring overnight at room temperature, the solvents were removed by rotary evaporation to give Q-1 as a brown semi-solid. Data for Q-1: 1H NMR (500 MHz, CDCl3) delta 2.01 (s, 3H), 4.71 (br s, 2H), 6.57 (s, 1H).
	With triethylamine; In methanol; at 20℃; for 12h;	Compound 3 was obtained as per reported method by stirring 1 with 2 at room temperature in the presence of triethylamine and was used without purification for further steps

	With methanol; triethylamine; at 20℃;	Intermediate compound 12 (Scheme 1B) was prepared by a 2-step procedure reported by Taylor et al.?2 Acetol 10 was condensed with malononitrile in the presence of triethylamine in methanol to afford 2-amino-3-cyano-4-methylfuran (compound 11) which was condensed with guanidine hydrochloride in presence of sodium methoxide to give intermediate (compound 12) in 44% yield. The synthesis of target compounds 2-9, outlined in Scheme 1B, involved oxidative thiolation of the common intermediate 2,4-diamino-5 -methyl-pyrrolo [2,3-d]pyrimidine (compound 12) with appropriately substituted thiols. Compounds 2-5 were synthesized from compound 12 with slight modification of the oxidative thiolation previously reported by Gangjee et al.?3 This procedure involved reacting compound l2with appropriately substituted thiols and iodine in a 2:1 mixture of ethanol and water at reflux to give compounds 2-5. Compounds 6-9 were synthesized by methylation of the pyrrole nitrogen using sodium hydride and iodomethane.
	With triethylamine; at 20℃; for 12h;	To a solution ofacetol (10 g, 135 mmol) in methanol (200 mL) at room temperaturewas added malononitrile (8.9 g, 135 mmol) and triethylamine(13.7 g, 135 mmol). The resulting mixture was stirred at room temperatureovernight. The reaction mixture was then stripped of solventin vacuo. The residue was washed with hexane-ethyl acetate(5:1) (250 mL 5). The resulting hexane-ethyl acetate solution ofthe product was collected. After the evaporation of solvent underreduced pressure, 13 g (79%) of the crude product was obtainedas an orange powder and was used directly in the next reactionwithout analysis.

References: [1]Chemical and pharmaceutical bulletin,1985,vol. 33,p. 937 - 943.
[2]Patent: US2004/14755,2004,A1 .Location in patent: Page/Page column 18-19.
[3]Patent: US2008/132490,2008,A1 .Location in patent: Page/Page column 23.
[4]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1684 - 1701.
[5]Patent: US2010/10016,2010,A1 .Location in patent: Page/Page column 14-15.
[6]Patent: WO2016/22890,2016,A1 .Location in patent: Page/Page column 44.
[7]Journal of Medicinal Chemistry,2016,vol. 59,p. 5752 - 5765.
[8]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2640 - 2650.

10
[ 123-75-1 ]
[ 116-09-6 ]
[ 54151-38-1 ]
[ 231610-09-6 ]

Yield	Reaction Conditions	Operation in experiment
	at 20℃;

References: [1]Yaylayan, Varoujan A.; Harty-Majors, Susan; Ismail, Ashraf A. [Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 6, p. 2335 - 2340].

11
[ CAS Unavailable ]
[ 497-04-1 ]
[ 2134-29-4 ]
[ 116-09-6 ]
[ 96-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	With (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; copper dichloride; 6,6,6-trifluoro-1-phenylhexane-1,3,5-trione In tetrahydrofuran at 25℃;

References: [1]El-Qisairi, Arab; Henry, Patrick M. [Journal of Organometallic Chemistry, 2000, vol. 603, # 1, p. 50 - 60].

12
[ 116-09-6 ]
[ 1099-45-2 ]
[ 10150-93-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With manganese(IV) oxide In dichloromethane at 20℃; for 24h;
54%	With manganese(IV) oxide In dichloromethane at 20℃; for 16h;

References: [1]Runcie, Karen A.; Taylor, Richard J. K. [Chemical Communications, 2002, # 9, p. 974 - 975].
[2]Weinstein, Adam B.; Ellman, Jonathan A. [Organic Letters, 2016, vol. 18, # 13, p. 3294 - 3297].

13
[ 87165-53-5 ]
[ 116-09-6 ]
[ 579471-57-1 ]

Yield	Reaction Conditions	Operation in experiment
43%	With calcium sulfate; silver(l) oxide In dichloromethane at 20℃; for 10h;

References: [1]Ohno, Hiroaki; Wakayama, Ryutaro; Maeda, Shin-ichiro; Iwasaki, Hiroki; Okumura, Mitsuaki; Iwata, Chuzo; Mikamiyama, Hidenori; Tanaka, Tetsuaki [Journal of Organic Chemistry, 2003, vol. 68, # 15, p. 5909 - 5916].

14
[ 116-09-6 ]
[ 147-85-3 ]
[ 25343-57-1 ]
[ 54151-38-1 ]
[ 55041-86-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 0.52% 2: 0.14% 3: 0.03%	With sodium hydrogensulfite at 130℃; for 0.333333h;

References: [1]Adams, An; Tehrani, Kourosch Abbaspour; Kersiene, Milda; De Kimpe, Norbert [Journal of Agricultural and Food Chemistry, 2004, vol. 52, # 18, p. 5685 - 5693].

15
[ 114046-25-2 ]
[ 116-09-6 ]
3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)butan-2-one [ No CAS ]
(3S,4R)-3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)-butan-2-one [ No CAS ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 5965 - 5967.

16
[ 513-86-0 ]
[ 5077-67-8 ]
[ 116-09-6 ]
[ 108-95-2 ]
[ 3131-63-3 ]
[ 3782-00-1 ]
[ 4265-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	8percent Mo on gamma-alumina containing 1-2percent dispersed silica; at 145℃; for 2h;Conversion of starting material;	[0032] A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm of 3-hydroxy-2-butanone (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 8 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 98, 98, and 100 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. Approximately 6 percent of the HA was converted to 2-methyl benzofuran, 3 percent of the 1-HB was converted to 2-ethyl benzofuran, and 3 percent of 3-HB was converted to 1,3-dimethyl benzofuran.
	gamma-alumina Containing 1-2percent Dispersed Silica; at 145℃; for 2h;Conversion of starting material;	[0034] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing no molybdenum and which had been previously activated and dried. Conversion of hydroxyketones were 18, 15, and 8 percent for HA, 1HB, and 3HB, respectively. The corresponding benzofuran selectivities were approximately 2, 0.5, and 2 percent.
	4percent Mo on gamma-alumina Containing 1-2percent Dispersed Silica; at 145℃; for 2h;Conversion of starting material;	[0033] A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm 3-hydroxy-2-butanone (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 4 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 84, 87 and 98 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 6, 3, and 2.5 percent.

	at 145℃; for 2h;Conversion of starting material;	[0035] A feed containing 990 ppm HA, 520 ppm of 1HB and 490 ppm of 3HB was prepared from pure phenol and heated for 2 hours at 145° C. without addition of a catalyst. Conversion of hydroxyketones averaged 5, 5, and 7 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 3, 0.1, and 3 percent.
	at 145℃; for 2h;Conversion of starting material;	A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm of 3- HYDROXY-2-BUTANONE (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145 C with an alumina catalyst containing approximately 8 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 98,98, and 100 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. Approximately 6 percent of the HA was converted to 2-methyl benzofuran, 3 percent of the 1-HB was converted to 2-ethyl benzofuran, and 3 percent of 3-HB was converted to 1,3- dimethyl benzofuran.
	aluminum oxide; at 145℃; for 2h;Conversion of starting material;	A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145 C with an alumina catalyst containing no molybdenum and which had been previously activated and dried. Conversion of hydroxyketones were 18,15, and 8 percent for HA, 1HB, and 3HB, respectively. The corresponding benzofuran selectivities were approximately 2,0. 5, and 2 percent.
	at 145℃; for 2h;Conversion of starting material;	A feed containing 990 ppm hydroacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 490 ppm 3-hydroxy- 2-butanone (3HB or acetoin), was prepared from pure phenol and contacted for 2 hours at 145°C with an alumina catalyst containing approximately 4 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 84,87 and 98 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 6,3, and 2.5 percent.
	at 145℃; for 2h;Conversion of starting material;	A feed containing 990 ppm HA, 520 ppm of 1HB and 490 ppm of 3HB was prepared from pure phenol and heated for 2 hours at 145 C without addition of a catalyst. Conversion of hydroxyketones averaged 5,5, and 7 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 3,0. 1, and 3 percent.

References: [1]Patent: US2004/158106,2004,A1 .Location in patent: Page 3.
[2]Patent: US2004/158106,2004,A1 .Location in patent: Page 3.
[3]Patent: US2004/158106,2004,A1 .Location in patent: Page 3.
[4]Patent: US2004/158106,2004,A1 .Location in patent: Page 3.
[5]Patent: WO2004/72009,2004,A1 .Location in patent: Page 10.
[6]Patent: WO2004/72009,2004,A1 .Location in patent: Page 11.
[7]Patent: WO2004/72009,2004,A1 .Location in patent: Page 11.
[8]Patent: WO2004/72009,2004,A1 .Location in patent: Page 11.

17
[ 513-86-0 ]
[ 5077-67-8 ]
[ 116-09-6 ]
[ 3131-63-3 ]
[ 3782-00-1 ]
[ 4265-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	amberlyst 15 (TM) cation exchange resin; at 80℃; for 2h;Conversion of starting material;	[0046] A feed containing 1450 ppm hydroxyacetone (HA or acetol), 520 ppm of 1-hydroxy-2-butanone (1HB), and 540 ppm of 3-hydroxy-2-butanone (3HB or acetoin) was prepared from pure phenol. The feed was stirred for 2 hours at 80° C. with Amberlyst 15 (TM) cation exchange resin beads which had previously been water rinsed and vacuum dried. Conversion of the hydroxyketones was 94 percent for HA, 74 percent for 1HB, and 80 percent for 3HB. Approximately 6 percent of the HA was converted to 2-MBF (2-methyl benzofuran), 3 percent of the 1HB was converted to EBF (2-ethyl benzofuran), and 24 percent of the 3HB was converted to DMBF (1,3 dimethyl benzofuran).
	Y-zeolite catalyst; at 150℃; for 2h;Conversion of starting material;	[0047] A feed containing 1000 ppm HA, 5300 ppm of 1HB, and 1050 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 150° C. with a Y-zeolite catalyst which had been previously activated and dried. The percent conversions of hydroxyketones were 93 for HA, 84 for 1HB, and 89 for 3HB. The corresponding benzofuran selectives were 33, 18 and 68 percent.
	alumina catalyst containing approximately 4 percent molybdenum; at 145℃; for 2h;Conversion of starting material;	[0049] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 4 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones were 84, 87 and 98 percent for HA, 1HB, and 3HB. The corresponding benzofuran selectivities averaged approximately 6, 3, and 2.5 percent.

	alumina catalyst containing approximately 8 percent molybdenum; at 145℃; for 2h;Conversion of starting material;	[0048] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing approximately 8 percent molybdenum. The catalyst was previously activated and dried. Conversion of hydroxyketones averaged 98, 98, and 100 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 6, 3, and 3 percent
		[0050] A feed containing 990 ppm HA, 520 ppm of 1HB, and 490 ppm of 3HB was prepared from pure phenol and contacted for 2 hours at 145° C. with an alumina catalyst containing no molybdenum and which had been previously activated and dried. Conversion of hydroxyketones averaged 18, 15, and 8 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities were approximately 2, 0.5, and 2 percent.
	Conversion of starting material;	[0051] A feed containing 990 ppm HA, 520 ppm of 1HB and 490 ppm of 3HB was prepared from pure phenol and heated for 2 hours at 145° C. without addition of a catalyst. Conversion of hydroxyketones averaged 5, 5, and 7 percent for HA, 1HB, and 3HB, respectively, for three separate experiments. The corresponding benzofuran selectivities averaged approximately 3, 0.1, and 3 percent.

References: [1]Patent: US2004/158105,2004,A1 .Location in patent: Page 5.
[2]Patent: US2004/158105,2004,A1 .Location in patent: Page 5.
[3]Patent: US2004/158105,2004,A1 .Location in patent: Page 5.
[4]Patent: US2004/158105,2004,A1 .Location in patent: Page 5.
[5]Patent: US2004/158105,2004,A1 .Location in patent: Page 5.
[6]Patent: US2004/158105,2004,A1 .Location in patent: Page 5.

18
[ 125314-13-8 ]
[ 116-09-6 ]
[ 396091-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	With NaCNBH₃ In tetrahydrofuran; dichloromethane	15 Synthesis of 3-(1-methylindol-3-yl)-4-[3-(2-hydroxy-1-methylethylamino)phenyl]-1H-pyrrole-2,5-dione Example 15 Synthesis of 3-(1-methylindol-3-yl)-4-[3-(2-hydroxy-1-methylethylamino)phenyl]-1H-pyrrole-2,5-dione To a mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.32 mmol) and hydroxyacetone (0.03 mL, 1.5 eq) in CH2Cl2 (12 mL) and THF (5 mL) was added NaCNBH3 (28 mg, 1.5 eq) and the reaction mixture was stirred overnight. The volatiles were removed under vacuo and the residue was purified by preparatory TLC to give 3-(1 -methylindol-3-yl)-4-[3-(2-hydroxy-1-methylethylamino)phenyl]- 1H-pyrrole-2,5 -dione(8 mg). LC/MS: M+ 375(85.6%).

References: [1]Current Patent Assignee: F HOFFMANN LA ROCHE - US2002/52397, 2002, A1.

19
[ CAS Unavailable ]
[ 116-09-6 ]
[ 693-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; hydrogen isocyanide In <i>N</i>,<i>N</i>-dimethyl-aniline; 1,2-dichloro-benzene	25 EXAMPLE 25 EXAMPLE 25 13.5 Parts of hydrogen cyanide are passed into a solution of 65 parts of 2-octanol in 45 parts by volume of o-dichlorobenzene at 0° C., and 20 parts of hydrogen chloride are then passed in at +20° C., whilst cooling. The viscous mixture is stirred for 30 minutes at 20° C. 18.5 parts of hydroxyacetone and 91 parts of N,N-dimethylaniline are then added at +10° C. and the mixture is heated at 75° C. for 1 hour. At the same temperature, 150 parts of 20% strength by weight aqueous sodium hydroxide solution are added, the mixture is cooled to room temperature, the organic phase is separated off and the 4-methyloxazole formed is distilled at atmospheric pressure (boiling point 88° C.). Yield: 10.4 parts (50% of theory).

References: [1]Current Patent Assignee: BASF - US4039554, 1977, A.

20
[ 116-09-6 ]
[ 693-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-diethylaniline	1.b EXAMPLE 1 b. Preparation of 4-methyloxazole: the hydrochloride obtained is added a little at a time to a solution of 29 parts of hydroxyacetone and 180 parts of N,N-diethylaniline at from 15° to 20° C. The mixture is then slowly heated to 90° C. and the 4-methyloxazole formed is distilled at 20 mm Hg into a cooled receiver. Fractional distillation gives 14.5 parts (44% of theory) of 4-methyloxazole of boiling point 88° - 89° C.
	With hydrogenchloride; hydrogen isocyanide In <i>N</i>,<i>N</i>-dimethyl-aniline; nitrobenzene; cyclohexanol	24 EXAMPLE 24 EXAMPLE 24 13.5 Parts of hydrogen cyanide are passed into a solution of 50.1 parts of cyclohexanol is 45 parts by volume of nitrobenzene at 0° C. and 20 parts of hydrogen chloride are then passed in at +20° C., whilst cooling. The resulting suspension is stirred for 30 minutes at 20° C. 18.5 parts of hydroxyacetone in 91 parts of N,N-dimethylaniline are then added at +10° C. and the mixture is heated to 75° C. At the same time the 4-methyl-oxazole formed is distilled at 20 mm Hg into a cooled receiver. 11.5 parts (55% of theory) of 4-methyloxazole, of boiling point 88° C., are obtained.

References: [1]Current Patent Assignee: BASF - US4039554, 1977, A.
[2]Current Patent Assignee: BASF - US4039554, 1977, A.

21
[ 583-59-5 ]
[ 116-09-6 ]
[ 693-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen isocyanide In dichloromethane; <i>N</i>,<i>N</i>-dimethyl-aniline	23 EXAMPLE 23 EXAMPLE 23 13.5 Parts of hydrogen cyanide are passed into a solution of 57 parts of 2-methylcyclohexanol in 135 parts by volume of methylene chloride at -10° C., and 20 parts of hydrogen chloride are then passed in at +20° C., whilst cooling. The mixture is stirred for 45 minutes at room temperature. Methylene chloride is then stripped off under reduced pressure until the residue is viscous but can still be stirred. 18.5 parts of hydroxyacetone and 91 parts of N,N-dimethylaniline are added at +10° C. and the mixture is heated to 75° C. At the same time the 4-methyloxazole formed, and the residual methylene chloride, are distilled under reduced pressure into a cooled receiver. 15.8 parts (76% of theory) of 4-methyloxazole, of boiling point 88° C., are obtained after fractional distillation.

References: [1]Current Patent Assignee: BASF - US4039554, 1977, A.

22
[ CAS Unavailable ]
[ 116-09-6 ]
[ 693-93-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-diethylaniline	2.b EXAMPLE 2 b. Preparation of 4-methyloxazole: 32.7 parts of formimido-cyclohexyl ester hydrochloride are added, a little at a time, to a solution of 7.4 parts of hydroxyacetone and 45 parts of N,N-diethylaniline at 15° C. The mixture is slowly heated to 70° C. and the 4-methyloxazole formed is distilled at 20 mm Hg into a cooled receiver. Yield 5 parts (60% of theory) of 4-methyloxazole of boiling point 88° - 89° C.
	With 1-methyl-pyrrolidin-2-one; N,N-diethylaniline	29 EXAMPLE 29 EXAMPLE 29 16.4 Parts of formimido-cyclohexyl ester hydrochloride are introduced into a solution of 3.7 parts of hydroxyacetone, 14.9 parts of N,N-diethylaniline and 25 parts of N-methylpyrrolidone at -25° C. The mixture is then heated to 70° C and the 4-methyloxazole formed is distilled at C. 20 mm Hg into a cooled receiver. Yield, 4.7 parts (56% of theory), of boiling point 88° C.

References: [1]Current Patent Assignee: BASF - US4039554, 1977, A.
[2]Current Patent Assignee: BASF - US4039554, 1977, A.

23
[ CAS Unavailable ]
[ 116-09-6 ]
[ 693-93-6 ]

Yield	Reaction Conditions	Operation in experiment
		21.b EXAMPLE 21 b. Preparation of 4-methyloxazole: a mixture of 6.4 parts of formimido-cyclohexyl ester and 3.7 parts of hydroxy-acetone is heated to 150° C. in the course of 30 minutes. At the same time the 4-methyloxazole formed is distilled off. 0.5 part of 4-methyloxazole of boiling point 88.5° C. is obtained.
	With chloroacetic acid	22 EXAMPLE 22 EXAMPLE 22 A mixture of 6.4 parts of formimido-cyclohexyl ester, 4.75 parts of chloroacetic acid and 3.7 parts of hydroxyacetone is heated at 60° C. for 1 hour. At the same time the 4-methyloxazole formed is distilled at 20 mm Hg into a cooled receiver. After fractionation, 1.2 parts (27% of theory) of 4-methyloxazole of boiling point 88° C. are obtained.

References: [1]Current Patent Assignee: BASF - US4039554, 1977, A.
[2]Current Patent Assignee: BASF - US4039554, 1977, A.

24
[ 116-09-6 ]
[ 122-51-0 ]
[ 109-77-3 ]
[ 5117-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; acetic anhydride; acetic acid; triethylamine; In toluene;	EXAMPLE 1 This Example illustrates the preparation of a number of 4-amino-5-methyl-furo [2,3-d] pyrimidines having the structural formula: STR5 The supposed 2-amino-3-cyano-4-methylfuran (m.p. 156-8) described by Gewalt (Chem. Ber., 1966, 99, 1002) has been shown by McKee (J. Org. Chem., 1973, 38, 612) to be the Diels-Alder dimer, 2,4-diamino-3,5-dicyano-3a,6-dimethyl-3a,4,7,7a-tetrahydro-endo-4,7-epoxybenzofuran. A mixture of malononitrile (17.9 g), triethylamine (14.6 ml) and toluene (140 ml) was stirred at room temperature for ten minutes, then treated with acetol (13.2 g). Following an exothermic reaction, the mixture was refluxed for ten minutes, cooled and the toluene layer decanted. The oily residue was extracted with toluene and the total extracts washed with water, dried and evaporated to give a white solid (7.24 g; m.p. 114). Recrystallisation from petroleum (b.p. 80-100) gave material m.p. 117, shown to be the unstable monomeric 2-amino-3-cyano-4-methylfuran by analysis and by n.m.r. spectrometry [CDCl3:tau3.43 (1H, singlet); 5.0 (2H, broad); 8.03 (3H, singlet]. A mixture of this freshly prepared material (3.12 g), triethylorthoformate (3.0 ml) and acetic anhydride (0.5 ml) was heated for two and a half hours at 130, then treated with a mixture of an appropriate primary amine (0.028 mole, approximately 10% excess), acetic acid (5 ml) and anhydrous sodium acetate (3.1 g). The mixture was heated at 130 for a further three hours, cooled, poured into water and extracted with ether. The extracts were washed with water, dried and evaporated and the residue distilled in a bulb-tube apparatus (pressure, ~0.02 mm; bath temperature 130-170) to give products as shown in Table II below. In most cases, the distillate solidified and was recrystallized from e.g. petroleum to give material with the melting-point shown. Compound No. 9 was made similarly.

References: [1]Patent: US4199584,1980,A .

25
[ 497-09-6 ]
[ 116-09-6 ]
[ 32589-20-1 ]

References: [1]Chemistry - A European Journal,2011,vol. 17,p. 2623 - 2632.

26
[ 50-99-7 ]
[ 67-63-0 ]
[ 67-56-1 ]
[ 57-55-6 ]
[ 623-61-0 ]
[ 107-21-1 ]
[ 116-09-6 ]
[ 67-64-1 ]
[ 56-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 300 - 375℃; Autoclave;	3 Example 3; Various batch reactions using the Materials of Example 2 were completed. Table 2 presents the yields of products according to the methods of the invention generated from several simple sugars. In these runs aqueous solutions of the sugar at room temperature were pumped into the hot alcohol under pressure.

References: [1]Current Patent Assignee: IOWA STATE UNIVERSITY OF SCIENCE AND TECHNOLOGY - US2011/137085, 2011, A1 Location in patent: Page/Page column 9.

27
[ 50-99-7 ]
[ 67-63-0 ]
[ 67-56-1 ]
[ 96-26-4 ]
[ 108-21-4 ]
[ 623-61-0 ]
[ 107-21-1 ]
[ CAS Unavailable ]
[ 116-09-6 ]
[ 67-64-1 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 300℃; for 0.3h; Stainless steel flow reactor;	4 Example 4; Continuous reactions using the Materials of Example 2 were completed. The yields of products obtained from a continuous run are presented in Table 3. A reaction mixture under high pressure (from approximately 1500 psi to 3500 psi) was pumped sequentially through a high temperature zone (from approximately 200° C. to 325° C.), a heat exchanger, a backpressure regulator, and then into a collection vessel. The reaction mixture was generated by pumping an aqueous solution of glucose at room temperature into a heated source of 2-propanol (temperature from approximately 275° C. to 325° C.) which was being pumped into the high temperature zone. aContinuous reaction pumped through a stainless steel tube having about a 5 min residence time and a length to diameter ratio of about 20. Temperature was 300° C., and the sample was collected over a period of 18 min. Glucose input during this time was 0.64 g and solvent included 32 mL of 2-propanol/5% water. ball yields given in grams per gram starting material cDetected by NMR in the D2O solution as the hydrate but reported as the aldehyde. disopropyl ester tentatively assigned as isopropyl glycolate eisopropyl ester tentatively assigned as isopropyl acetate funidentified products not soluble in alcohol gunidentified products soluble in alcohol htotal identified products derived from carbohydrate material iproduced by the oxidation of 2-propanol

References: [1]Current Patent Assignee: IOWA STATE UNIVERSITY OF SCIENCE AND TECHNOLOGY - US2011/137085, 2011, A1 Location in patent: Page/Page column 9-10.

28
[ 67-63-0 ]
[ 57-50-1 ]
[ 67-56-1 ]
[ 57-55-6 ]
[ 108-21-4 ]
[ 623-61-0 ]
[ 107-21-1 ]
[ 116-09-6 ]
[ 67-64-1 ]
[ 56-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 300 - 375℃; Autoclave;	3 Example 3; Various batch reactions using the Materials of Example 2 were completed. Table 2 presents the yields of products according to the methods of the invention generated from several simple sugars. In these runs aqueous solutions of the sugar at room temperature were pumped into the hot alcohol under pressure.

References: [1]Current Patent Assignee: IOWA STATE UNIVERSITY OF SCIENCE AND TECHNOLOGY - US2011/137085, 2011, A1 Location in patent: Page/Page column 9.

29
[ 57-48-7 ]
[ 67-63-0 ]
[ 67-56-1 ]
[ 57-55-6 ]
[ 623-61-0 ]
[ 107-21-1 ]
[ 116-09-6 ]
[ 67-64-1 ]
[ 56-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 300 - 375℃; Autoclave;	3 Example 3; Various batch reactions using the Materials of Example 2 were completed. Table 2 presents the yields of products according to the methods of the invention generated from several simple sugars. In these runs aqueous solutions of the sugar at room temperature were pumped into the hot alcohol under pressure.

References: [1]Current Patent Assignee: IOWA STATE UNIVERSITY OF SCIENCE AND TECHNOLOGY - US2011/137085, 2011, A1 Location in patent: Page/Page column 9.

30
[ 1001756-21-3 ]
[ 116-09-6 ]
[ 1455035-91-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium hydroxide In tetrahydrofuran at 20℃; for 1h;	34 Synthesis of 7-chloro-2-methyl[1,6]naphthyridin-3-ol Treat a mixture of 4-amino-6-chloro-pyridine-3-carbaldehyde (39 g, 0.25 mol) and 2-hydroxy acetone (28 g, 0.375 mol) in THF (400 mL) with KOH (52.5 g, 0.75 mol), stir at RT for 1 h, add water and acidify with IN HC1. Collect the resulting solids by filtration, wash with water (3x), then EtOAc (2x) and dry to afford the title compound (45 g, 93%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.00 (s, 1 H), 7.77 (s, 1 H), 7.53 (s, 1 H), 2.54 (s, 3 H).
93%	With potassium hydroxide In tetrahydrofuran at 20℃; for 1h;

References: [1]Current Patent Assignee: ELI LILLY - WO2013/134298, 2013, A1 Location in patent: Page/Page column 45.
[2]Henry, James R.; Kaufman, Michael D.; Peng, Sheng-Bin; Ahn, Yu Mi; Caldwell, Timothy M.; Vogeti, Lakshminarayana; Telikepalli, Hanumaiah; Lu, Wei-Ping; Hood, Molly M.; Rutkoski, Thomas J.; Smith, Bryan D.; Vogeti, Subha; Miller, David; Wise, Scott C.; Chun, Lawrence; Zhang, Xiaoyi; Zhang, Youyan; Kays, Lisa; Hipskind, Philip A.; Wrobleski, Aaron D.; Lobb, Karen L.; Clay, Julia M.; Cohen, Jeffrey D.; Walgren, Jennie L.; McCann, Denis; Patel, Phenil; Clawson, David K.; Guo, Sherry; Manglicmot, Danalyn; Groshong, Chris; Logan, Cheyenne; Starling, James J.; Flynn, Daniel L. [Journal of Medicinal Chemistry, 2015, vol. 58, # 10, p. 4165 - 4179].

31
[ 96042-30-7 ]
[ 116-09-6 ]
[ 74685-00-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dmap; triethylamine In water	96 1-(tert-butyldimethylsilyloxy)propan-2-one Example 96 1-(tert-butyldimethylsilyloxy)propan-2-one To a DCM (5 mL) solution of 1-hydroxypropan-2-one (500 mg, 6.8 mmol), DMAP (41 mg, 0.34 mmol) and Et3N (1.2 mL, 8.16 mmol) was added TBSCl (1.133 g, 7.5 mmol) at 0° C. under nitrogen atmosphere. The mixture was stirred at r.t. for 2 h. Then the mixture was added water and extracted with EtOAc. The organic layer was purified by silica gel chromatography using PE/EA (10/1) to give the title compound (950 mg, 75%). EDI-MS (M+1): 189. 1H NMR (300 MHz, CDCl3) δ 4.057 (s, 2H), 2.080 (s, 3H), 0.832 (s, 9H), 0.001 (s, 6H).

References: [1]Current Patent Assignee: BIOGEN MA - US2014/100195, 2014, A1 Location in patent: Page/Page column.

32
[ 78-94-4 ]
[ 114794-47-7 ]
[ 57011-15-1 ]
[ 473-80-3 ]
[ 141-46-8 ]
[ 127-17-3 ]
[ 116-09-6 ]
[ 78-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxyl at 24.84℃;

References: [1]Schoene, Luisa; Schindelka, Janine; Szeremeta, Edyta; Schaefer, Thomas; Hoffmann, Dirk; Rudzinski, Krzysztof J.; Szmigielski, Rafal; Herrmann, Hartmut [Physical Chemistry Chemical Physics, 2014, vol. 16, # 13, p. 6257 - 6272].

33
[ 9004-34-6 ]
[ 57-55-6 ]
[ 2418-52-2 ]
[ 149-32-6 ]
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 69-65-8 ]
[ 50-70-4 ]
[ 107-21-1 ]
[ 116-09-6 ]
[ 56-81-5 ]