Thiophene-3-ol,tetrahydro-, (S)-
S-3-hydroxytetrahydrofuran
CAS: 86087-23-2;79107-75-8
Molecular Formula: C4H8O2
Thiophene-3-ol,tetrahydro-, (S)- - Names and Identifiers
Thiophene-3-ol,tetrahydro-, (S)- - Physico-chemical Properties
| Molecular Formula | C4H8O2 |
| Molar Mass | 88.11 |
| Density | 1.103 g/mL at 25 °C (lit.) |
| Boling Point | 80 °C/15 mmHg (lit.) |
| Specific Rotation(α) | 18.5 º (c=2 MeOH) |
| Flash Point | 175°F |
| Water Solubility | soluble |
| Solubility | Chloroform, Methanol (Slightly) |
| Vapor Presure | 47Pa at 25℃ |
| Appearance | Liquid |
| Specific Gravity | 1.11 |
| Color | Clear colorless to pale yellow |
| BRN | 4652609 |
| pKa | 14.49±0.20(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | n20/D 1.45(lit.) |
| Physical and Chemical Properties | Appearance colorless transparent liquid boiling range ℃(15mmHg) 79-80 |
Thiophene-3-ol,tetrahydro-, (S)- - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| UN IDs | NA 1993 / PGIII |
| WGK Germany | 3 |
| HS Code | 29321900 |
Thiophene-3-ol,tetrahydro-, (S)- - Reference Information
| LogP | -0.784 at 22℃ and pH6.8 |
| surface tension | 72mN/m at 1g/L and 25 ℃ |
| introduction | (S)-( )-3-hydroxytetrahydrofuran is a colorless to pale yellow transparent liquid and can be used as a chemiluminescence analysis and detection reagent. |
| Uses | The synthesis of the anti-AIDS drug Ampunavir requires two important intermediates, one of which is (S)-() -3-Hydroxytetrahydrofuran. It can be synthesized by asymmetric borohydride or hydrosilicide of dihydrofuran, asymmetric hydrogenation reduction of 4-chloro3-carbonylbutyrate-intramolecular etherification, enzymatic resolution of 3-hydroxytetrahydrofuran racemate, etc. In most cases, the optical purity of the product is not enough. (S)-( )-3-hydroxytetrahydrofuran can be used as an intermediate of afatinib for the first-line treatment of advanced non-small cell lung cancer (NSCLC) and HER2-positive advanced breast cancer patients. |
| prepare | prepare dimethyl L-malate 2: dissolve 30gL-malic acid (0.224mol) in 90ml methanol, cool to -10 ℃, add 39ml dichlorosulfoxide (0.55mol) dropwise under stirring, and finish dropwise for 1.5h. Stir for 4h at room temperature, then heat reflux for 1h to stop the reaction. Concentrate under reduced pressure, add 125ml of 20% sodium carbonate solution, and adjust pH = 7. Extraction with ethyl acetate 3 times, 100ml each time. The ethyl acetate layer was combined, anhydrous magnesium sulfate was dried and concentrated under reduced pressure to obtain 33.68g of colorless oily liquid with 93% yield. Preparation of butyl alcohol 3:32.4gL-malate dimethyl ester (0.2mol) dissolved in 100ml methanol, adding 8.48g potassium borohydride (0.16mol) and 17g lithium chloride (0.4mol), heating reflux. After that, 4.24g of potassium borohydride (0.08mol) will be added every 20min for a total of 5 times. After the addition of continuous reflux for 3h,TLC detection of no raw material point, stop the reaction. A large amount of solid is filtered and removed first, the pH value of the filtrate is adjusted to 3 with sulfuric acid, the precipitated solid is filtered and removed again, and concentrated under reduced pressure. The resulting solid-liquid mixture was diluted, stirred, and filtered with 20ml of ethyl acetate and 20ml of ethanol. The filtrate is concentrated under reduced pressure to obtain 21g of yellow viscous liquid. Preparation of (S)-( )-3-hydroxytetrahydrofuran 4: The crude product obtained in the previous step was added to 2g(0.01mol) of p-toluenesulfonic acid monohydrate, dissolved by heating and continued to heat up to 200 ℃. Decompression fractionation (87 ℃/22mmHg), 7.6g of yellow oily liquid was collected, and the two-step yield was 43%. |
Last Update：2024-04-09 21:11:58
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