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(Nippon Zeon Co., Ltd., Japan) Jpn. Kokai Tokkyo Koho JP 2000044555, 2000
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Aldrich: 4-benzyloxyindole (1 g), $A225; 4-hydroxyindole (1 g), $A288 (1/2003). A patent describing an efficient synthesis of 4-hydroxyindoles from cyclohexane-1,3-dione, where the key step is the reaction of oxochromancarboxylic acid derivatives with ammonia in methanol in an autoclave, has been filed. The author notes that this may effect the price of 4-hydroxyindoles in the future. Matsuura, T. (Nippon Zeon Co., Ltd., Japan) Jpn. Kokai Tokkyo Koho JP 2000044555, 2000.
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Smith, A.L.1
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0141709207
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note
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Preparation of 14 g of 3 was performed in our laboratories using standard glassware.
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28
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0141820521
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note
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This substitution reaction was accomplished successfully using an aqueous solution of N,N-dimethylamine with no formation of 3-butyn-1-ol detected by NMR. Previous methods have used N,N-dimethylamine as a gas or dissolved in an organic solvent; both of these sources of N,N-dimethylamine are considerably more expensive or inconvenient to use.
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29
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0141597518
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note
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4OH) to give the title compound as a light brown oil in 69% yield (2.45 g, 6.3 mmol).
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