| Identification | More | [Name]
Ethyl 2,2-diethoxyethylcyanoacetate | [CAS]
52133-67-2 | [Synonyms]
AKOS 92469
ETHYL 2,2-DIETHOXYETHYLCYANOACETATE
ETHYL 2-CYANO-4,4-DIETHOXYBUTANOATE
ETHYL 2-CYANO-4,4-DIETHOXYBUTYRATE
ETHYL-2,2-DIETHOXYTHYLCYANOACETATE
Ethyl-2-Cyano-4,4-Diethoxybutanoide | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C11H19NO4 | [MDL Number]
MFCD02094250 | [Molecular Weight]
229.27 | [MOL File]
52133-67-2.mol |
| Safety Data | Back Directory | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN3276 | [HazardClass ]
6.1 | [HS Code ]
2926907090 |
| Hazard Information | Back Directory | [Chemical Properties]
Colourless Liquid | [Uses]
Ethyl 2-Cyano-4,4-diethoxybutyrate (cas# 52133-67-2) is a compound useful in organic synthesis. | [Synthesis]
Method AI: Synthesis of ethyl 2-cyano-4,4-diethoxybutyrate (xlii-a): In a dry reaction flask, ethyl 2-cyanoacetate (11.4 g, 101 mmol, 5.0 eq.), potassium carbonate (2.8 g, 20 mmol, 1.0 eq.), and sodium iodide (200 mg, 1.3 mmol, 0.06 eq.) were added in sequence. Subsequently, 2-bromo-1,1-diethoxyethane (4 g, 20 mmol, 1.0 eq.) was slowly added to the mixture. The reaction mixture was refluxed at 145°C for 4 hours with reference to J. Chem. Soc., 1960,131-138. After completion of the reaction, it was cooled to room temperature and the product was purified by silica gel column chromatography with petroleum ether/ethyl acetate as eluent (gradient elution: 80:1→40:1→40:1) to give 3.57 g of the target compound xii-a as a colorless oil in 78% yield.1H NMR (400 MHz, CDCl3): δ 4.70 (t, J=5.6 Hz, 1H), δ 4.26 (q, J=7.2Hz, 2H), 3.78-3.64 (m, 3H), 3.62-3.45 (m, 2H), 2.35-2.14 (m, 2H), 1.34 (q, J=7.2Hz, 3H), 1.25-1.16 (m, 6H). | [References]
[1] Patent: US2015/307477, 2015, A1. Location in patent: Paragraph 1563
[2] Patent: JP6121658, 2017, B2. Location in patent: Paragraph 1270; 1271
[3] Archiv der Pharmazie, 2018, vol. 351, # 8,
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 12, p. 4064 - 4067
[5] Organic Letters, 2017, vol. 19, # 9, p. 2214 - 2217 |
|
|