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Microwave Assisted Wolff-Kishner Reduction Reaction
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Abstract
A Wolff-Kishner reduction of a carbonyl group was carried out in a household microwave oven. Isatin was first converted to the hydrazone with 55% hydrazine and ethylene glycol by irradiation in the microwave oven at medium power for 30 seconds. Then, isatin 3-hydrazone was mixed with ethylene glycol and potassium hydroxide and irradiated in the microwave oven for only 10 seconds. After simple work-up and recrystallization, oxindole was obtained in a yield of 32.4%. The two step syntheses described here offer several advantages: (1) very short reaction time with no need for special microscale glassware, (2) mild experimental conditions (hot oil baths and heating mantles are not required), (3) the reagents are easy to handle (students do not need to prepare sodium ethoxide from sodium metal and absolute ethanol).
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
SynthesisCiting Articles
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This article has been cited by 9 ACS Journal articles (5 most recent appear below).
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- Received: August 03, 2009
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