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ChemicalBook--->CAS DataBase List--->230642-84-9

230642-84-9

230642-84-9 Structure

230642-84-9 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H319-H315-H335
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313P-P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362
[HS Code ]

2932990090
Hazard InformationBack 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]

4-Benzofuranethanol, 2,3-dihydro-, 4-(4-methylbenzenesulfonate)

230642-83-8

4-vinyl-2,3-dihydrobenzofurane

230642-84-9

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
Spectrum DetailBack Directory
[Spectrum Detail]

4-vinyl-2,3-dihydrobenzofurane(230642-84-9)1HNMR
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