Exp102

=Objective= To accomplish a Friedel-Crafts tert-butylation of [|N-(2-furylmethyl)acetamide] with tert-butanol. [Exp105, [|Iovel 1998]]

=Procedure= [|N-(2-furylmethyl)acetamide] (562.8mg, 2.88mmol, 103A) 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.

=Results= [|H NMR] (Prepared in Exp 103) [|H NMR] (12min) [|H NMR] (48min) [|H NMR] (17h 13min) [|H NMR] (20h 55min including 5h reflux) [|H NMR] (2days)
 * N-(2-furylmethyl)acetamide**
 * 102A (40uL in CDCl3)**

=Discussion= 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 ([|Iovel 1998]) as result of which the furan ring may have opened up.

=Conclusion= The reaction has been aborted.

=Log=

2007-06-05
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 **102A** 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)

2007-06-06
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.

2007-06-07
11:12 Obtained H NMR by dissolving 150uL of 102A in CDCl3 (800uL) (2days)


 * References**
 * 1) Exp105
 * 2) [|I. Iovel'. et.al] Chemistry of Heterocyclic Compounds; Vol.34, Iss.1.pp 1-12

=Tags= [|N-(2-furylmethyl)acetamide]: [|InChI=1/C7H9NO2/c1-6(9)8-5-7-3-2-4-10-7/h2-4H,5H2,1H3,(H,8,9)]

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