METHYL 2-(3-HYDROXYPROP-1-YNYL)BENZOATE Chemical Properties

storage temp. 

2-8°C

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

METHYL 2-(3-HYDROXYPROP-1-YNYL)BENZOATE Usage And Synthesis

Synthesis

Example 1: Preparation of tert-butoxy-[4-(4-methoxy-3,5-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl]-acetic acid Step A: Synthesis of methyl 2-(3-hydroxyprop-1-ynyl)-benzoate Methyl 2-iodobenzoate (88.0 g, 335.9 mmol), 2-propyn-1-ol (28.3 g, 503.8 mmol), copper iodide (1.2 g, 6.7 mmol), Pd(PPh3)2Cl2 (7.0 g, 10.0 mmol), and triethylamine (68.0 g, 671.8 mmol) were suspended in acetonitrile (1 L). The solution was bubbled with N2 for 20 min to deoxidize. Subsequently, the reaction mixture was stirred at reflux for 3 h under N2 protection. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by column chromatography to afford the target product methyl 2-(3-hydroxyprop-1-ynyl)-benzoate (58.8 g, 92.0% yield). 1H NMR (400 MHz, d6-DMSO): δ 2.48 (t, J = 6.2 Hz, 1H), 3.88 (s, 3H), 4.52 (d, J = 5.6 Hz, 2H), 7.32 (t, J = 7.6 Hz, 1H), 7.41 (t, J = 7.6 Hz, 1H), 7.51 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 7.6 Hz, 1H), 7.90 (d, J = 7.6 Hz, 1H). 7.90 (d, J = 7.2 Hz, 1H).

References

[1] Patent: WO2012/102985, 2012, A1. Location in patent: Page/Page column 94
[2] Doklady Chemistry, 1985, vol. 283, p. 212 - 214
[3] Dokl. Akad. Nauk SSSR Ser. Khim., 1985, vol. 283, # 3, p. 630 - 633
[4] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 996 - 1005
[5] Organic Letters, 2018, vol. 20, # 10, p. 3034 - 3038

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