A Scalable, One-Pot Synthesis of 1,2,3,4,5-Pentacarbomethoxycyclopentadiene.,Synthesis

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A Scalable, One-Pot Synthesis of 1,2,3,4,5-Pentacarbomethoxycyclopentadiene.
Synthesis ( IF 2.2 ) Pub Date : 2019-03-01 , DOI: 10.1055/s-0037-1611650
M Alex Radtke ₁ , Caroline C Dudley ₂ , Jacob M O'Leary ₂ , Tristan H Lambert _{1,

2}

Affiliation

1,2,3,4,5-Pentacarbomethoxycyclopentadiene (PCCP) is a strong organic acid and a precursor to useful organocatalysts, including chiral Brønsted acids and silicon-based Lewis acids. The synthetic route to PCCP, first reported in 1942, is inconvenient for a number of reasons. The two-step synthesis requires the purification of intermediates from intractable side-products, high reaction temperatures, and extensive labor (3 days). We have developed an improved procedure that delivers PCCP efficiently in 24 hours in one pot at ambient temperature and without isolation.

中文翻译：

1,2,3,4,5-五碳甲氧基环戊二烯的可规模化一锅法合成。

1,2,3,4,5-五碳甲氧基环戊二烯 (PCCP) 是一种强有机酸，也是有用有机催化剂的前体，包括手性布朗斯台德酸和硅基路易斯酸。PCCP 的合成路线于 1942 年首次报道，但由于多种原因并不方便。两步合成需要从棘手的副产物中纯化中间体、高反应温度和大量的劳动力（3天）。我们开发了一种改进的程序，可在环境温度下在一锅中 24 小时内高效地提供 PCCP，且无需隔离。

更新日期：2019-01-22

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