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| | (R)-(-)-3-Hydroxytetrahydrofuran Basic information |
| | (R)-(-)-3-Hydroxytetrahydrofuran Chemical Properties |
| alpha | -18.5 º (c=2 MeOH) | | Boiling point | 181 °C (lit.) | | density | 1.097 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.45(lit.) | | Fp | 180 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform, Methanol (Slightly) | | pka | 14.49±0.20(Predicted) | | form | Liquid | | color | Clear colorless | | Specific Gravity | 1.097 | | Optical Rotation | [α]20/D 18°, c = 2.4 in methanol | | InChI | InChI=1S/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2/t4-/m1/s1 | | InChIKey | XDPCNPCKDGQBAN-SCSAIBSYSA-N | | SMILES | O1CC[C@@H](O)C1 | | CAS DataBase Reference | 86087-24-3(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | NA 1993 / PGIII | | WGK Germany | 3 | | HazardClass | CBL | | HS Code | 29321900 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | (R)-(-)-3-Hydroxytetrahydrofuran Usage And Synthesis |
| Chemical Properties | Colorless to light yellow liqui | | Uses | (R)-(-)-3-Hydroxytetrahydrofuran is used as a chemical reactant in the synthesis of pharmaceutical agents. Empagliflozin is synthesized using this reactant | | Uses | (R)-(-)-3-Hydroxytetrahydrofuran may be used as building block in the synthesis of potent HIV protease inhibitors. | | Synthesis | Example 5 Preparation of (R)-3-hydroxytetrahydrofuran: 35 g (0.28 mol) of (R)-4-chloro-1,3-butanediol made in reference to Example 2 was dissolved in 70 mL of 0.5 N hydrochloric acid solution and the reaction was heated under reflux conditions for 2 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was neutralized with 50% aqueous sodium hydroxide solution, followed by evaporation under reduced pressure to remove water. To the residual crystals and oily mixture, 60 mL of methanol was added and mixed with thorough stirring. Insoluble crystals were removed by filtration and the filtrate was concentrated under reduced pressure. Finally, the concentrated residue was distilled under reduced pressure to give 16.6 g of (R)-(-)-3-hydroxytetrahydrofuran in the form of colorless liquid (purity: 99.1%; yield: 67%). Its rotundity was determined as [α]D23 = -15.91° (c = 2.45, methanol). | | References | [1] Patent: US5780649, 1998, A
[2] Patent: WO2008/93955, 2008, A1. Location in patent: Paragraph 65-66
[3] Patent: WO2016/21192, 2016, A1. Location in patent: Paragraph 0085 |
| | (R)-(-)-3-Hydroxytetrahydrofuran Preparation Products And Raw materials |
| Raw materials | 3-Furanol, tetrahydro-, 3-acetate-->Dihydrofuran-3(2H)-one-->3-Hydroxytetrahydrofuran-->(R)-4-CHLORO-1,3-BUTANEDIOL-->(R)-(+)-1,2,4-BUTANETRIOL-->but-3-en-1-yl 4-methylbenzene-1-sulfonate-->(S)-1,2,4-Butanetriol-->2,3-Dihydrofuran-->n-Butane-->Hydrochloric acid | | Preparation Products | Furan, tetrahydro-3-iodo-, (3S)--->(S)-3-P-MESYLOXYTETRAHYDROFURAN |
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