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Quality Control of [ 6946-10-7 ] Purity: 98% SDS Specification

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Product Details of [ 6946-10-7 ]

CAS No. :	6946-10-7
Formula :	C₇H₁₀O₅
M.W :	174.15
SMILES Code :	O=C(COC(C)=O)COC(C)=O
English Name :	2-Oxopropane-1,3-diyl diacetate
MDL No. :	MFCD01310655
InChI Key :	PZVCVSQSQHGBNE-UHFFFAOYSA-N
Pubchem ID :	243418

Safety of [ 6946-10-7 ]

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Application In Synthesis of [ 6946-10-7 ]

* 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 [ 6946-10-7 ]

[ 6946-10-7 ] Synthesis Path-Downstream 1~14

1
[ 96-26-4 ]
[ 108-24-7 ]
[ 6946-10-7 ]

Yield	Reaction Conditions	Operation in experiment
82.7%	With pyridine In acetone at 20℃; for 16h;	1 [00738] 1,3-DG-acetate (Int-284): [00739] To a solution of 1,3-dihydroxypropan-2-one (5.0 g, 55.5 mmol) and acetic anhydride (11.33 g, 111.07 mmol) in acetone (50ml) was added pyridine (9.66g, 122.18 mmol) and the reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solution evaporated under vacuum, redissolved in DCM (50 ml) and washed with 1N HCl (50 ml), water (50ml). The combined organic layer was dried over sodium sulphate and evaporated under vacuum to get crude. The crude material was purified by column chromatography using 100-200 mesh silica gel, and the desired product was eluted at 25% ethyl acetate/hexane to afford 2-oxopropane-1,3-diyl diacetate (8.0g, 82.7%). 1H NMR (400 MHz, CDCl3) δ 4.79(s, 4H), 2.21 (s, 6H).
82.7%	With pyridine In acetone at 20℃; for 16h;	1 [00738] 1,3-DG-acetate (Int-284): [00739] To a solution of 1,3-dihydroxypropan-2-one (5.0 g, 55.5 mmol) and acetic anhydride (11.33 g, 111.07 mmol) in acetone (50ml) was added pyridine (9.66g, 122.18 mmol) and the reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the solution evaporated under vacuum, redissolved in DCM (50 ml) and washed with 1N HCl (50 ml), water (50ml). The combined organic layer was dried over sodium sulphate and evaporated under vacuum to get crude. The crude material was purified by column chromatography using 100-200 mesh silica gel, and the desired product was eluted at 25% ethyl acetate/hexane to afford 2-oxopropane-1,3-diyl diacetate (8.0g, 82.7%). 1H NMR (400 MHz, CDCl3) δ 4.79(s, 4H), 2.21 (s, 6H).
81%	With pyridine at 20℃; for 3h; Inert atmosphere; Large scale reaction;

78%	With pyridine at 15 - 22℃; for 3.08333h;	1 A 16 L reactor equipped with a mechanical stirrer, a Pt-100 thermometer, a reflux condenser and a nitrogen inlet was charged with 1.00 kg (10.9 mol) 1,3-dihydroxyacetone and 3.25 L (4.03 mol) pyridine. To this suspension 3.31 L (34.8 mol) acetic acid anhydride was added during 35 min, maintaining the temperature between 15 and 22° C. with a cooling bath. During the addition the suspension turned into a clear, slightly reddish solution. The mixture was stirred for 2.5 h at RT before it was concentrated on a rotatory evaporator at 50-55° C./10 mbar. The oily residue was dissolved in 10.0 L dichloromethane and washed two times with 5.0 L 2N hydrochloric acid, then with 5.0 L water. The organic layer was concentrated on a rotatory evaporator at 40° C./10 mbar and the oily residue was further dried under these conditions for 1.5 h. The dark red crude product (2 kg) was dissolved in 5.7 L toluene and the solution was warmed to 30° C. 5 L heptane were added during 10 min and the resulting turbid solution was seeded with product crystals, whereas fast crystallization occurred. 5 L heptane was added to the suspension to improve stirability. After stirring overnight at RT the suspension was cooled to 0° C. and stirred for 2 h at that temperature. The crystals then were filtered off and washed portionwise with totally 7 L of pre-cooled heptane. The crystals were dried at 30-35° C. at <=10 mbar over the weekend, to give 1.47 kg 1,3-diacetoxyacetone (78% yield; assay: 100%).
	With pyridine
	With pyridine; dmap at 20℃;
	With pyridine at 20℃; for 1.5h;
	With pyridine; dmap for 2.5h; Inert atmosphere;	1,3-Bis(acetoxy)propan-2-one (21) To a stirred solution of dihydroxyacetone (20.0 g, 0.22 mol) in pyridine (300 mL) was added DMAP (1.4 g, 11.8 mmol, 5 mol%) and acetic anhydride (63 mL, 0.66 mmol, 3 eq.) under argon. After 2 h 30 the solvent was removed under reduced pressure and the mixture was diluted with CH2Cl2 (300 mL). The organic layer was washed with HCl (3N) until pH = 5, with NaHCO3 until pH = 7 and then with water (50 mL). The organic layer was dried over MgSO4, filtered and evaporated under reduced pressure. The crude product was used without further purification. Yield: 90 % as a pale yellow oil
	With pyridine at 0 - 20℃; for 16h;	1.2; 4 Step 2: Synthesis of 2-oxopropane-l,3-diyl diacetate To a solution of l,3-dihydroxypropan-2-one (90 g, 999 mmol) in pyridine (400 ml) was added acetic anhydride (408 g, 3997 mmol) at 0 °C. After the resulting mixture was stirred at 20 °C for 16 hours, it was concentrated under reduced pressure. The residue was diluted with DCM (1000 mL), washed with 2N HC1 (2 x 1000 mL), NaHC03 (3 x 1000 mL). The combined organic layers was dried with anhydrous Na2S04, filtered, and concentrated under reduced pressure. The residue was poured into stirring petroleum ether (1500 mL), the product was precipitated out and filtered to give 2-oxopropane-l,3-diyl diacetate. H- MR: (300 MHz, CDC13, ppm): δ 4.76 (s, 4H), 2.18 (s, 6H).

References: [1]Current Patent Assignee: MONASH UNIVERSITY - WO2021/159021, 2021, A1 Location in patent: Paragraph 00738-00739.
[2]Current Patent Assignee: MONASH UNIVERSITY - WO2021/159021, 2021, A1 Location in patent: Paragraph 00738-00739.
[3]Location in patent: experimental part Adam, Jean-Michel; Foricher, Joseph; Hanlon, Steven; Lohri, Bruno; Moine, Gerard; Schmid, Rudolf; Wirz, Beat; Zutter, Ulrich; Stahr, Helmut; Weber, Martin [Organic process research and development, 2011, vol. 15, # 3, p. 515 - 526].
[4]Current Patent Assignee: HOFFMANN LA ROCHE - US2006/270853, 2006, A1 Location in patent: Page/Page column 6; 11.
[5]Fischer,H.O.L.; Feldmann [Chemische Berichte, 1929, vol. 62, p. 862].
[6]Fischer,H.O.L.; Mildbrand [Chemische Berichte, 1924, vol. 57, p. 709].
[7]Yasohara, Yoshihiko; Miyamoto, Kenji; Kizaki, Noriyuku; Hasegawa, Junzo; Ohashi, Takehisa [Tetrahedron Letters, 2001, vol. 42, # 19, p. 3331 - 3333].
[8]Location in patent: experimental part Lange, Kathrin; Koenig, Andreas; Roegler, Carolin; Seeling, Andreas; Lehmann, Jochen [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 3141 - 3144].
[9]Novoa, Alexandre; Pellegrini-Moïse, Nadia; Bourg, Stéphane; Thoret, Sylviane; Dubois, Joëlle; Aubert, Genevive; Cresteil, Thierry; Chapleur, Yves [European Journal of Medicinal Chemistry, 2011, vol. 46, # 9, p. 3570 - 3580].
[10]Current Patent Assignee: MERCK SHARP DOHME - WO2017/53216, 2017, A2 Location in patent: Page/Page column 34; 40-41.

2
[ 89727-88-8 ]
[ 108-24-7 ]
[ 6946-10-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	In pyridine for 14h; Ambient temperature;
85%	With pyridine
80%	With pyridine at 20℃;	To a thin slurry of dihydroxyacetone dimer vi in pyridine (5 equiv) was slowly added acetic anhydride (4.1 equiv) at RT. The resulting solution was aged overnight, diluted with CH2Cl2 (10 vol) and quenched by adding cold 6N HCl (5-6 equiv). The aqueous layer was separated and back extracted with CH2Cl2 (2x 3 vol). The combined organic layer was neutralized with 15% aqueous K2CO3 to bring the pH to 7, washed with brine, dried with MgSO4, filtered and concentrated. The crude product was crystallized from toluene: heptane to afford the desired product in 80% isolated yield as white solid.

77%	In pyridine
76%	With pyridine In dichloromethane Inert atmosphere;
76%	With pyridine at 20℃;

References: [1]Suemune; Mizuhara; Akita; Sakai [Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 8, p. 3440 - 3444].
[2]Chao, Qi; Nair, Vasu [Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 9, p. 1199 - 1202].
[3]Current Patent Assignee: MERCK - WO2009/54887, 2009, A1 Location in patent: Page/Page column 48.
[4]Mori, Kenji [Tetrahedron, 2014, vol. 70, # 35, p. 5752 - 5762].
[5]Weinstabl, Harald; Suhartono, Marcel; Qureshi, Zafar; Lautens, Mark [Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308][Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4].
[6]Qureshi, Zafar; Weinstabl, Harald; Suhartono, Marcel; Liu, Hongqiang; Thesmar, Pierre; Lautens, Mark [European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069].

3
[ 867-13-0 ]
[ 6946-10-7 ]
[ 77356-33-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydride In tetrahydrofuran for 12h; Ambient temperature;
82%	Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 1h; Stage #2: 1,3-diacetoxyacetone In tetrahydrofuran at 0 - 20℃; for 12h;
	With sodium hydride 1.) THF, 1 h, room temp., 2.) THF, 0.5 h, room temp., 0.5 h, reflux; Yield given. Multistep reaction;

References: [1]Balasubramaniam, Rajiv P.; Moss, David K.; Wyatt, Justin K.; Spence, John D.; Gee, Arvin; Nantz, Michael H. [Tetrahedron, 1997, vol. 53, # 22, p. 7429 - 7444].
[2]Fort, Diego A.; Woltering, Thomas J.; Nettekoven, Matthias; Knust, Henner; Bach, Thorsten [Chemical Communications, 2013, vol. 49, # 29, p. 2989 - 2991].
[3]Harrison, Timothy; Myers, Peter L.; Pattenden, Gerald [Tetrahedron, 1989, vol. 45, # 16, p. 5247 - 5262].

4
[ 6946-10-7 ]
[ 33420-49-4 ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With diethylamino-sulfur trifluoride at 20℃; for 96h;	46.a (46a) 2,2-difluoropropane-1,3-diyl diacetate A mixture of 2-oxopropane-1,3-diyl diacetate (10.6 g, 60.8 mmol) and diethylaminosulfur trifluoride (24.2 ml, 182 mmol) was stirred at room temperature for 4 days. The reaction mixture was diluted with ethyl acetate, which was cooled on ice, and then a saturated sodium bicarbonate solution was added and the organic layer was taken out. The organic layer was washed twice with water, dried over magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure to obtain the title compound (10.92 g, 91.6%). 1H NMR(400 MHz, CDCl3) δppm; 2.13(6H, s), 4.35(4H, t, J=12 Hz).
69%	With diethylamino-sulfur trifluoride for 48h;	59 Compound 59I: 2,2-Difluoropropane-1 ,3-diolA solution of acetic acid 3-acetoxy-2-oxopropyl ester (6.2 g, 35.6 mmol) in DAST (1 1 mL) was stirred for 48h. The reaction mixture was added to a mixture of ice and sat. sodium carbonate drop wise. The aq. layer was extracted with ethyl acetate (3x100 mL). The combined organic layers were dried over Na2S04, filtered and concentrated to give 4.8 g (69%) of acetic acid 3-acetoxy-2,2-difluoro-propyl ester which was dissolved in methanol and treated with NaOMe (3.9 g, 73 mmol). After 6h, the reaction mixture was neutralized with amberlite IR ion exchange resin (acidic). The resulting mixture was filtered and the filtrate was concentrated to 2.8 g (70%) of desired product as an oil. 1H NMR (500 MHz, CDCI3) δ 3.91 (t, J = 12.5 Hz, 4H), 1.8 (bs, 2H).
9.54 g	With diethylamino-sulfur trifluoride at 22℃; for 48h;

With diethylamino-sulfur trifluoride at 20℃; for 48h; Sealed vessel;

1.H A solution of compound lh-1 (9g, 51.7mmol) and DAST in a sealed vessel was stirred at room temperature for 2 days. The reaction mixture was diluted with EtOAc and added slowly to a cold sat. aq. sodium bicarbonate solution. The mixture was stirred at room temperature for 15min. The separated organic layer was washed with brine, dried (Na2S04) and concentrated to dryness to give the crude lh.

References: [1]Current Patent Assignee: EISAI R D MANAGEMENT - US2007/10542, 2007, A1 Location in patent: Page/Page column 70.
[2]Current Patent Assignee: OSI PHARMACEUTICALS - WO2012/74951, 2012, A1 Location in patent: Page/Page column 135.
[3]Starrett, John E.; Tortolani, David R.; Russell, John; Hitchcock, Michael J. M.; Whiterock, Valerie; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 12, p. 1857 - 1864].
[4]Current Patent Assignee: ENANTA PHARMACEUTICALS - WO2011/49908, 2011, A2 Location in patent: Page/Page column 86-87.

5
[ 816-39-7 ]
[ CAS Unavailable ]
[ 6946-10-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetrabutylammomium bromide In benzene for 24h; Ambient temperature;

References: [1]Valentin, Marie-Lise; Bolte, Jean [Bulletin de la Societe Chimique de France, 1995, vol. 132, p. 1167 - 1172].

6
[ 6946-10-7 ]
[ 41162-17-8 ]
[ 189625-08-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium hydride In tetrahydrofuran

References: [1]Diaz-Cortes, Reyna; Silva, Ana L.; Maldonado, Luis A. [Tetrahedron Letters, 1997, vol. 38, # 13, p. 2207 - 2210].

7
[ 6946-10-7 ]
[ 1015-28-7 ]
[ 189625-09-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride In tetrahydrofuran

References: [1]Diaz-Cortes, Reyna; Silva, Ana L.; Maldonado, Luis A. [Tetrahedron Letters, 1997, vol. 38, # 13, p. 2207 - 2210].

8
[ 6946-10-7 ]
[ 189625-07-8 ]
[ 189625-10-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydride In tetrahydrofuran

References: [1]Diaz-Cortes, Reyna; Silva, Ana L.; Maldonado, Luis A. [Tetrahedron Letters, 1997, vol. 38, # 13, p. 2207 - 2210].

9
[ 6946-10-7 ]
[ 213530-03-1 ]
[ 209912-19-6 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydride In tetrahydrofuran at 25℃; for 2h;