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Ugi NMR Analysis
To accomplish a Friedel-Crafts tert-butylation of
with tert-butanol. [
) was added to t-butanol (15mL) with concentrated sulfuric acid (1 mL). The reaction mixture was stirred overnight at room temperature. After 20h of stirring at room temperature it was refluxed for 5 hours.
(Prepared in Exp 103)
102A (40uL in CDCl3)
(20h 55min including 5h reflux)
The reaction mixture after two days (including 5h reflux) does not seem to contain a desired quantity of the tert-butylated product. This maybe because of acidophobic character of furan (
) as result of which the furan ring may have opened up.
The reaction has been aborted.
16:30 Distilled 100ml of tert-butyl alcohol at 82C (data not recorded)
19:47 Added N-(2-furylmethyl)acetamide, freshly distilled tert-butanol (15ml) and conc. sulfuric acid in a round bottom flask. The reaction mixture was constantly stirred on a stir plate.This is
19:57 Removed 40uL of 102A, dissolved it in CDCl3 (800uL) and obtained H NMR (12min)
20:35 Obtained H NMR by dissolving 40uL of 102A in CDCl3 (800uL). (48min)
13:00 Obtained H NMR by dissolving 40uL of 102A in CDCl3 (800uL) (17h 13min)
15:50 Started refluxing the reaction mixture. (
note time turned heat on and setting on mantle then note time when refluxed observed to start - at least one drop per 2-3 sec
16:42 Obtained H NMR by dissolving 150uL of 102A in CDCl3 (800uL) (20h 55min)
20:00 Turned the heat off.
11:12 Obtained H NMR by dissolving 150uL of 102A in CDCl3 (800uL) (2days)
I. Iovel'. et.al
Chemistry of Heterocyclic Compounds; Vol.34, Iss.1.pp 1-12
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