Synthesis of Ethyl 2-Methylene-3-aryl-4-oxoalkanoates and Ethyl 2-Arylidene-4-oxoalkanoates from the Baylis—Hillman Acetates.
✍ Scribed by Jeong Mi Kim; Yang Jin Im; Taek Hyeon Kim; Jae Nyoung Kim
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 31 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0931-7597
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## Abstract Ethyl 4‐oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 Å in almost quantitative yield with 3‐aminopropanol and 2‐aminoethanol to form the bicyclic lactams __rac__‐2 and __rac__‐3, respectively. Surprisingly, the (±)‐5‐alkyl‐4‐oxa‐1‐azab
## Abstract Reaction of ethyl 2‐(3‐pyridyl)acetate **4a** or ethyl 2‐methyl‐2‐(3‐pyridyl)acetate **4b**, with phenyl chloroformate or methyl chloroform ate, afforded the intermediate pyridinium salt **5** which undergoes regioselective nucleophilic attack at C‐4 upon reaction with a Grignard reagen