Identification | Back Directory | [Name]
4-vinyl-2,3-dihydrobenzofurane | [CAS]
230642-84-9 | [Synonyms]
4-Vinyl-2,3-dihydrobenzofuran 4-ethenyl-2,3-dihydrobenzofuran Benzofuran, 4-ethenyl-2,3-dihydro- 4-ethenyl-2,3-dihydro-1-benzofuran 4-Vinyl-2,3-dihydrobenzofuran(VBF) Imtermediate tasimelteon(4-ethenyl-2,3-dihydrobenzofuran) | [EINECS(EC#)]
607-194-1 | [Molecular Formula]
C10H10O | [MDL Number]
MFCD09030659 | [MOL File]
230642-84-9.mol | [Molecular Weight]
146.19 |
Chemical Properties | Back Directory | [Boiling point ]
244.3±25.0 °C(Predicted) | [density ]
1.078±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [Appearance]
Colorless to light yellow Liquid |
Hazard Information | Back Directory | [Uses]
4-Vinyl-2,3-dihydrobenzofuran is an intermediate in the synthesis of tasimelteon (T007740). Tasimelteon is a novel drug, used in the treatment of non-24 hour sleep-wake disorder. It helps to correct the circadian rhythm disorder often seen in patients who are visually impaired. | [Synthesis]
General procedure for the synthesis of 4-vinyl-2,3-dihydrobenzofuran from the compound (CAS: 230642-83-8): dissolve toluene sulfonate of part C (100 g, 314 mmol) in THF (1200 mL) in a 2000 mL three-necked round-bottomed flask equipped with a mechanical stirrer, a digital thermometer, and a homogeneous-pressure charging funnel. Room temperature was maintained. The reaction mixture was cooled to 0 °C via an ice water bath. A THF solution of t-BuOK (1 M, 345.5 mL) was slowly added dropwise at 0 °C for 110 min. The reaction mixture was gradually warmed to ambient temperature and stirring was continued for 2 hours. Upon completion of the reaction, water (350 mL) and EtOAc (600 mL) were added to separate the organic and aqueous layers. The aqueous layer was further extracted with EtOAc (2 x 150 mL). All EtOAc layers were combined, washed with brine (2 × 150 mL), dried over MgSO4 and filtered. The solvent was removed by distillation under reduced pressure to give 46 g of the target product 4-vinyl-2,3-dihydrobenzofuran in 100% yield. | [References]
[1] Patent: EP1041980, 2005, B1. Location in patent: Page/Page column 33 [2] Journal of Chemical Research, 2016, vol. 40, # 11, p. 667 - 669 [3] Patent: CN106542973, 2017, A. Location in patent: Paragraph 0098-0101 |
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