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Synlett 2004(4): 631-634  
DOI: 10.1055/s-2004-817749
LETTER
© Georg Thieme Verlag Stuttgart · New York

Neutral, Metal-free Hydration of Alkynes Using Microwave Irradiation in ­Superheated Water

Anil Vasudevan*, Mary K. Verzal
Medicinal Chemistry Enabling Technologies, Abbott Laboratories, R4CP, AP10, 100 Abbott Park Road, Abbott Park, IL 60064, USA
Fax: +1(847)935-0310; e-Mail: Anil.Vasudevan@abbott.com;
Further Information

Publication History

Received 19 December 2003
Publication Date:
10 February 2004 (online)

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Abstract

A novel methodology for the hydration of alkynes in superheated water using microwave irradiation is reported. Extension of this methodology to hydroamination of alkynes is also described.

Key words

microwave - alkynes - hydration - superheated water

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  • 19a

    Typical Procedure for the Hydration of Alkynes: A suspension of the alkyne in a mixture of the alkyne (0.1 mol) and 3 mL water in a sealed reaction vial was heated at 200 °C in an Emrys® synthesizer for 20 min, following which the sample was cooled using compressed air. The product usually separated from the water on standing or could be extracted using 3 mL diethyl ether to afford the desired ketones in yields described in Table [2] , which demonstrated purity and analytical data consistent with commercial products.

  • 19b

    Typical Procedure for the Hydroamination of Alkynes: A mixture of the alkyne (0.87 mmol), amine (0.87 mmol) and water (3 mL) in a sealed reaction vial was heated at 200 °C in an Emrys® synthesizer for 20 min, following which the sample was cooled using compressed air. The product was extracted using diethyl ether (3 mL) to afford 0.23 g of 12 (ref. 17).

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