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Chemical Structure| 221121-37-5 Chemical Structure| 221121-37-5

Structure of 221121-37-5

Chemical Structure| 221121-37-5

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Product Details of [ 221121-37-5 ]

CAS No. :221121-37-5
Formula : C12H13FO3
M.W : 224.23
SMILES Code : O=C(OCC)CC(CC1=CC=C(F)C=C1)=O
MDL No. :MFCD03844416

Safety of [ 221121-37-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 221121-37-5 ]

* 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 [ 221121-37-5 ]

[ 221121-37-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 2033-24-1 ]
  • [ 64-17-5 ]
  • [ 459-04-1 ]
  • [ 221121-37-5 ]
YieldReaction ConditionsOperation in experiment
86.8% Example A7: A mixture of 4-fluorophenylacetyl chloride (4.91 g, 24.3 mmol), 2,2-dimethyl- 1,3-dioxane-4,6-dione (3.50 g, 24.3 mmol) and DIEA (5.84 g, 49.8 mmol) in DCM (30 mL)was stirred for 1 h at 0C, then warmed to RT for 2 h. The solution was diluted with DCM, washed with 0.1 N HC1 and brine, dried over Na2504 and evaporated to dryness. Theresulting orange solid was suspended in EtOH (100 mL) and refluxed for 2 hours. Thesolution was evaporated and the resulting orange oil was left in the freezer overnight to give a yellow solid. The crude solid was recrystallized from EtOH to afford ethyl 4-(4-fluorophenyl)-3 -oxobutanoate (5.3 g, 86.8% yield).
General procedure: To a stirred solution of substituted or unsubstituted phenylaceticacid (14ae14f) (5.0 mmol, 1.0 eq) in anhydrous dichloromethane(20 mL)was successively added oxalyl chloride (6.0 mmol,1.2 eq) and DMF (0.5 mmol, 0.1 eq) at 0 C under argon atmosphere.The resulting mixture was subsequently warmed up to roomtemperature and stirred for 6 h. The reaction mixture wasconcentrated in vacuum to afford the corresponding phenylacetylchloride. The solution of the corresponding phenylacetyl chloridein anhydrous dichloromethane (10 mL) was slowly added to astirred solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (5.0 mmol,1.0 eq), pyridine (10.0 mmol, 2.0 eq) in anhydrous dichloromethane(10 mL) at 0 C under argon atmosphere. The resulting mixture wassubsequently warmed up to room temperature and stirred for 5 h.The reaction mixture was concentrated and the resulting residuewas dissolved in anhydrous ethanol (20 mL), and the mixture washeated to 80 C for additional 4 h. After cooling, the mixture wasconcentrated to dryness and distributed inwater and ethyl acetate.The organic layer was separated and washed with water and brinesuccessively, dried over anhydrous sodium sulfate and concentratedin vacuum. The resulting residue was purified by silica gelchromatography (petroleum ether/ethyl acetate, v/v, 99:1 to 90:10)to give the desired product.5.1.1.1. Ethyl 4-(4-fluorophenyl)-3-oxobutanoate (16a). The titlecompound was prepared from 15a following general procedure A.Yield: 86%. 1H NMR (300 MHz, DMSO-d6) δ7.26e7.09 (m, 4H), 4.08(q, J 7.2 Hz, 2H), 3.88 (s, 2H), 3.66 (s, 2H), 1.17 (t, J 7.2 Hz, 3H).
  • 2
  • [ 2033-24-1 ]
  • [ 459-04-1 ]
  • [ 221121-37-5 ]
YieldReaction ConditionsOperation in experiment
86.8% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 3h; A mixture of 4-fluorophenylacetyl chloride (4.91 g, 24.3 mmol), 2,2- dimethyl- l ,3-dioxane-4,6-dione (3.50 g, 24.3 mmol) and DIEA (5.84 g, 49.8 mmol) in CH2C12 (30 mL) was stirred for 1 h at 0 C and at ambient temp for 2 h. The solution was diluted with CH2C12 (40 mL) and the organic phase was washed with 0.1 N HC1 and brine, dried over Na2S04 and evaporated to dryness. The resulting orange solid was suspended in EtOH (100 mL) and refluxed for 2 hours. The solution was evaporated and the resulting orange oil was left in the freezer overnight to give a yellow solid. The crude solid was recrystallized from EtOH to afford ethyl 4-(4-fluorophenyl)-3-oxobutanoate (5.3 g, 86.8% yield).
37% With pyridine; In dichloromethane; at 0℃; To a solution of 2,2-dimethyl-l,3-dioxane-4,6-dione (Meldrum's acid, 8.0 g, 56 mmol) dissolved in anhydrous methylene chloride (100 mL) and pyridine (11 mL), at 00C under nitrogen atmosphere, was slowly added 2-(4-fluorophenyl)acetyl chloride (7.6 mL, 9.6 g, 56 mmol). The red solution was stirred at 00C for 1.5 h. The reaction mixture was treated with 1 ν HCl (13 mL) and diluted with methylene chloride (200 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium chloride, dried and concentrated in vacuo to give 5-(2-(4- fluorophenyl)acetyl)-2,2-dimethyl-l,3-dioxane-4,6-dione. The crude intermediate was suspended in absolute ethanol (150 mL) and the resulting mixture was refluxed for 4 hours. The solvent was then removed in vacuo and the residue was purified by flash column chromatography (SiC^, 230-400 mesh, 8: 1 hexane-ethyl acetate gradient elution) to afford the desired product (4.6 g, 37%). 1H νMR (CDCl3) δ 7.23-7.15 (m, 2 H), 7.05-6.98 (m, 2 H), 4.18 (q, 2 H, J = 7.0 Hz), 3.81 (s, 2 H), 3.46 (s, 2 H), 1.26 (t, 3 H, J = 7.0 Hz); MS(ESI+) m/z 225 (M+H)+.
  • 3
  • [ 221121-37-5 ]
  • [ 1052114-81-4 ]
 

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