Structure of 614-99-3
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CAS No. : | 614-99-3 |
Formula : | C7H8O3 |
M.W : | 140.14 |
SMILES Code : | O=C(C1=CC=CO1)OCC |
MDL No. : | MFCD00003237 |
InChI Key : | NHXSTXWKZVAVOQ-UHFFFAOYSA-N |
Pubchem ID : | 11980 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.9% | With 5%-palladium/activated carbon; hydrogen; In ethanol; at 30 - 150℃; under 15001.5 Torr;Large scale; | 10359] 3010 g (21.5 mol) of thran-2-carboxylic acid ethyl ester, 500 ml of ethanol (1% MEK) and 20 g of catalyst, palladium on A-carbon dry, 5% Pd, type K-0227T) are initially introduced together and heated under a hydrogen pressure of 20 bat The reaction starts at 30-40C. and is relatively strongly exothermic. After 1-1.5 hat 60-70 C., the hydrogen absorption is as good as finished. The mixture is slowly heated to 140-150 C. and then stirred for a further 2-3 hat this temperature. GC control: starting material no longer present.10360] Filter off from the catalyst and concentrate the filtrate on a rotary evaporator (water bath: 60-70 C., 200-20 mbar). The crude yield is 3055 g.10361] The evaporated crude product is distilled with the addition of 0.1% by weight of Na2CO3 over a short column (b.p.: 9 1-93 C./40 mbar).10362] Yield: 2999 g (96.9% of theory)10363] ?H NMR (400 MHz, chioroform-d) oe 4.44 (dd, J=8.4, 5.2 Hz, 1H), 4.20 (qd, J=7.1, 1.7 Hz, 2H), 4.05-3.98 (m, 1H), 3.95-3.88 (m, 1H), 2.30-2.19 (m, 1H), 2.06-1.85 (m, 3H), 1.29 (t, J=7.1 Hz, 3H)10364] ?3C NMR (101 MHz, CDC13) oe 173.38, 76.80,69.33, 60.87, 30.20, 25.27, 14.24 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.98 g (88%) | With sodium; In ethanol; | EXAMPLE 51 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole-1-N-t-butyl carboxamide 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole was first prepared according to the procedure of Example 1B, using <strong>[136888-26-1]5,6-dichloro-4-azaoxindole</strong> (763 mg, 3.76 mmol), sodium (0.43 g, 18.8 mmol), ethyl-2-furoate (1.05 g, 7.5 mmol) and ethanol (25 mL). Yield: 0.98 g (88%). The title compound was prepared from 5,6-dichloro-3-(2-furoyl)-4-azaoxindole according to the procedure of Example 1C, using 5,6-dichloro-3-(2-furoyl)-4-azaoxindole (721 mg, 2.43 mmol), triethylamine (1.8 mL, 15.4 mmol), t-butyl isocyanate (1.4 mL, 12.3 mmol) and DMSO (20 mL). The reaction time was 22 hours. The crude product was triturated with methanol and recrystallized from hexane. Yield: 218 mg (23%). Analysis calc'd for C17 H15 Cl2 N3 O4: C 51.53, H 3.82, N 10.60. Found: C 51.70, H 3.81, N 10.57. M.p. 205-206 C. 1 H NMR (DMSO-d6) delta9.37 (br s, 1H), 8.32 (s, 1H), 7.91 (s, 1H), 7.85 (d, J=3.7 Hz, 1H), 6.69 (d, J=3.7 Hz, 1H), 1.38 (s, 9H). IR (KBr disc) 1730, 1620, 1605, 1590, 1555, 1535 cm-1. MS m/e (relative percent) 397(0.5), 395(2), 298(21), 296(33), 230(62), 228(100), 95(40). |
0.98 g (88%) | With sodium; In ethanol; | Example 51 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole-1-N-t-butyl carboxamide 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole was first prepared according to the procedure of Example 1B, using <strong>[136888-26-1]5,6-dichloro-4-azaoxindole</strong> (763 mg, 3.76 mmol), sodium (0.43 g, 18.8 mmol), ethyl-2-furoate (1.05 g, 7.5 mmol) and ethanol (25 mL). Yield: 0.98 g (88%). The title compound was prepared from 5,6-dichloro-3-(2-furoyl)-4-azaoxindole according to the procedure of Example 1C, using 5,6-dichloro-3-(2-furoyl)-4-azaoxindole (721 mg, 2.41 mmol), triethylamine (1.8 mL, 15.4 mmol), t-butyl isocyanate (1.4 mL, 12.3 mmol) and DMSO (20 mL). The reaction time was 22 hours. The crude product was triturated with methanol and recrystallized from hexane. Yield: 218 mg (23%). Analysis calc'd for C17H15Cl2N3O4: C 51.53, H 3.82, N 10.60. Found: C 51.70, H 3.81, N 10.57. M.p. 205 - 206C. 1H NMR (DMSO-d6) delta 9.37 (br s, 1H), 8.32 (s, 1H), 7.91 (s, 1H), 7.85 (d, J = 3.7 Hz, 1H), 6.69 (d, J = 3.7 Hz, 1H), 1.38 (s, 9H). IR (KBr disc) 1730, 1620, 1605, 1590, 1555, 1535 cmmin1. MS m/e (relative percent) 397(0.5), 395(2), 298(21), 296(33), 230(62), 228(100), 95(40). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; potassium carbonate; at 140℃; under 2250.23 Torr; for 4h;Autoclave; Sealed tube; | General procedure: Catalytic experiments were carried out in a 120 mL autoclaveequipped with a magnetic stirrer and automatic temperature control.After the FUR, Au catalyst, K2CO3 and the alcohol were added,the reactor was sealed, and purged with pure O2 for three times toremove the air. Then, the pressure of oxygen was charged to 0.3MPa and the reaction mixture was heated to 140 C and kept for4 h. When the reaction was finished, the solution was diluted withacetonitrile after the reactor was cooled to room temperature. Theproducts were qualitatively detected by an Agilent 7890A/5975Cgas chromatography-mass spectrometry (GC-MS). The conversionof FUR and selectivity of the product were quantitatively obtainedby GC instrument with the FID detector. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; potassium carbonate; calcium oxide; at 140℃; under 2250.23 Torr; for 4h;Autoclave; Sealed tube; | General procedure: Catalytic experiments were carried out in a 120 mL autoclaveequipped with a magnetic stirrer and automatic temperature control.After the FUR, Au catalyst, K2CO3 and the alcohol were added,the reactor was sealed, and purged with pure O2 for three times toremove the air. Then, the pressure of oxygen was charged to 0.3MPa and the reaction mixture was heated to 140 C and kept for4 h. When the reaction was finished, the solution was diluted withacetonitrile after the reactor was cooled to room temperature. Theproducts were qualitatively detected by an Agilent 7890A/5975Cgas chromatography-mass spectrometry (GC-MS). The conversionof FUR and selectivity of the product were quantitatively obtainedby GC instrument with the FID detector. |
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