Structure of 111-35-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 111-35-3 |
| Formula : | C5H12O2 |
| M.W : | 104.15 |
| SMILES Code : | OCCCOCC |
| English Name : | 3-Ethoxypropan-1-ol |
| MDL No. : | MFCD00002948 |
| InChI Key : | XHMWPVBQGARKQM-UHFFFAOYSA-N |
| Pubchem ID : | 8109 |
* 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 |
|---|---|---|
| With pyridine; phosphorus trichloride at 75℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 55% | With phosphorus tribromide In dichloromethane | 1.4 (4) (4) Production of 3-ethoxy-1-bromopropane Phosphorus tribromide (14.5 g) was slowly added dropwise to 16.8 g of 3-ethoxy-1-propanol. Thirty minutes later, the mixture was distilled in vacuo at 150° C. and 90 mmHg. Methylene chloride was added to the distillate, and the mixture was washed with a saturated sodium hydrogen carbonate aqueous solution. After drying, the solvent was removed, and the residue was distilled under reduced pressure to obtain 14.8 g of 3-ethoxy-1-bromopropane (4) having a purity of 94% (yield 55%). |
| 50% | With phosphorus tribromide at 0 - 20℃; | 27 4.1.27 1-Bromo-3-ethoxypropane (35) At 0°C phosphorus tribromide (4.33g, 16mmol, 1.0equiv) was added dropwise to 3-ethoxypropan-1-ol (4.90g, 47mmol, 2.9equiv). The mixture was stirred overnight at room temperature. After diluting with dichloromethane the mixture was washed with sat. NaHCO3 solution, dried over MgSO4. After filtration and evaporation of the solvent the product was obtained as a colorless oil (3.93g, 23.7mmol, 50%) [39]. 1H NMR (300MHz, CDCl3): δ=1.31 (t, J=7.2Hz, 3H), 2.03 (quint, J=6.2Hz, 2H), 3.39-3.49 (m, 6H). |
| With pyridine; phosphorus tribromide |
| With phosphorus tribromide | ||
| With pyridine; phosphorus tribromide |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 98% | With hydrogen at 95 - 100℃; | |
| With methanol; pumice stone; nickel at 45 - 100℃; Hydrogenation; | ||
| With hydrogen |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With ethanol; sodium | ||
| With methanol; copper chromite at 168 - 172℃; Hydrogenation; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen at 300℃; var. of catalyst, temp.; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In dichloromethane at 45℃; Yield given. Yields of byproduct given; | ||
| 1: 3 % Spectr. 2: 97 % Spectr. | In dichloromethane Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 91% | With sulfuric acid; hydrogen bromide for 10h; Heating; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 89% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With xylene at 115 - 120℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 3-ethoxy-1-propanol With triethylamine; trichlorophosphate In chloroform at 0 - 20℃; Stage #2: choline tosylate With pyridine In chloroform at 20℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Stage #1: 3-ethoxy-1-propanol; 2-(2-tert-butyldimethylsiloxyethyl)-4H-benzo[1,4]oxazin-3-one With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Stage #2: With methanesulfonic acid In methanol at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With hydrogen In ethanol at 20℃; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 52% | Stage #1: 3-ethoxy-1-propanol With sodium hydride In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 5-chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine-7-amine In dimethyl sulfoxide at 60℃; for 3h; |