Home Cart Sign in  
Chemical Structure| 64195-85-3 Chemical Structure| 64195-85-3
Chemical Structure| 64195-85-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of Ethyl 5-methyl-2,4-dioxohexanoate

CAS No. :64195-85-3
Formula : C9H14O4
M.W : 186.21
SMILES Code : CC(C)C(CC(C(OCC)=O)=O)=O
MDL No. :MFCD07323638

Safety of Ethyl 5-methyl-2,4-dioxohexanoate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Ethyl 5-methyl-2,4-dioxohexanoate

* 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 [ 64195-85-3 ]

[ 64195-85-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 64195-85-3 ]
  • [ 78208-72-7 ]
YieldReaction ConditionsOperation in experiment
56% With hydrazine hydrate; In ethanol; at 75℃; for 1h;Inert atmosphere; A mixture of compound 14-3 (1 g, 5.37 mmol) and hydrazine hydrate (10.7 mmol, 9.64 mol/L) in ethanol (20 mL) was stirred at 75 °C under N2 for 1 hour. After the reaction was complete, the mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V: V) = 2 : ito afford a pale yellow solid 14-4 (0.55 g, 56percent). MS (ESI, pos.ion) m/z: i83.i[M+1] and 1HNIVIR (600 MFIz, CDC13): (5 11.37 (b, iH), 6.63 (s, iH), 4.40?4.37 (m, 2H), 3.07?3.05 (m, iH), 1.43?1.40 (m, 3H), 1.39?1.30 (m, 6H) ppm.
54% With hydrazine hydrate; acetic acid; In ethanol; for 12h; a) Ethyl 5-isopropyl-lH-pyrazole-3-carboxylate To a solution of ethyl 4-methyl-3-oxopentanoate (4 g, 21.6 mmol, CAS: 7152-15-0) in ethanol (100 mL), was added acetic acid (1.9 g, 32.4 mmol) and hydrazine monohydrate (1.7 g, 0.032 mol, CAS: 7803-57-8). The reaction mixture was stirred for 12 hours until LCMS analysis indicated the completion of the reaction. The reaction solution was concentrated under reduced pressure and diluted with water. The mixture was extracted twice with dichloromethane (2 x 100 mL). The combined organic layers were washed with brine(40 mL), dried over Na2S04, filtered through thin silica pad, and concentrated under vacuum to give ethyl 5-isopropyl-lH-pyrazole-3- carboxylate (2.1 g, 54percent yield) as a yellow oil. MS (ESI): 183.2 (M+H)+.
With hydrazine; In ethanol; water; at 20℃; for 18h; Hydrazine hydrate (6.6 mL, 134 mmol) was added to a solution of 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (23.8 g, 188 mmol) in ethanol (100 mL) at RT under nitrogen. The reaction was allowed to proceed at RT for 18 h, and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane (300 mL) and water (300 mL) and the aqueous phase was removed. The organic phase was washed with water (2.x.200 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with a solvent gradient of pentane:ethyl acetate (4:1 changing to 2:1, by volume) to give the title product (18.9 g) as a white solid; 1H NMR (400 MHz, CDCl3): delta 10.80-10.95 (bs, 1H), 6.61 (s, 1H), 4.33-4.40 (quart, 2H), 2.98-3.08 (quin, 1H), 1.35-1.41 (t, 3H), 1.24-1.32 (d, 6H) ppm; LRMS (electrospray): m/z [M-H]+ 181.
YieldReaction ConditionsOperation in experiment
Preparation 2 5-Isopropyl-1H-pyrazol-3-carboxylic Acid Ethyl Ester Hydrazine hydrate (6.6 ml, 134 mmol) was added to a solution of the product from Preparation 1 (23.8 g, 188 mmol) in ethanol (100 ml) at room temperature under nitrogen. The reaction was allowed to proceed at room temperature for 18 h, and the solvent was removed under reduced pressure. The residue was partitioned between dichloromethane (300 ml) and water (300 ml) and the aqueous phase was removed. The organic phase was washed with water (2*200 ml), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluding with a solvent gradient of pentane:ethyl acetate (4:1 changing to 2:1, by volume) to give the title product (18.9 g) as a white solid; 1H NMR (400 MHz, CDCl3): delta=10.80-10.95 (1H, brs), 6.61 (1H, s), 4.33-4.40 (2H, quart), 2.98-3.08 (1H, quin), 1.35-1.41 (3H, t), 1.24-1.32 (6H, d) ppm; LRMS (electrospray): m/z [M-H]+181.
  • 3
  • [ 57508-48-2 ]
  • [ 64195-85-3 ]
  • 2-amino-6-isopropylpyridine-3,4-dicarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 74 mg of NaOEt in 1 mL of EtCH, is added 180 mg of 3-amino-3-imino-propanoic ethyl ester hydrochloride at room temperature, followed by addition of 200 mg of ethyl 5- methyl-2,4-dioxohexanoate. The reaction mixture is heated to reflux for 2 h. A total of 860 mg of 20% NaCH aq. solution is added under reflux. The reaction mixture is refluxed for another 1 h, and then cooled to room temperature. It is adjusted to pH = 5-6. The crude product is obtained by removing solvent completely, which is used to the next step directly. ?H NMR (400 MHz, D20 with NaCD): 8 6.63 (s, 1H), 2.88 (m, 1H), 1.25 (d, 6H); ?3C NMR (100 MHz, D20 with NaCD): 8 177.25, 173.83, 167.35, 156.79, 150.86, 111.87, 108.04, 35.25, 21.52; MS (m/z+1): 225.1.
 

Historical Records

Technical Information

Categories