Dolbier HW Solutions 553

Dolbier HW Solutions 553 - Ethyl acrylate (CH 2 ) 4 CH 3 O...

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Ammonia and its derivatives are very prone to react in this way; thus conjugate addition provides a method for the preparation of b -amino carbonyl compounds. ( a ) ( b ) ( c ) ( d ) The conjugate addition reaction that takes place in this case is an intramolecular one and occurs in virtually 100% yield. 22.43 The f rst step in the synthesis is the conjugate addition of methylamine to ethyl acrylate. Two sequential Michael addition reactions take place. CHCOCH 2 CH 3 CH 3 NHCH 2 CH 2 COCH 2 CH 3 CH 3 N(CH 2 CH 2 CO 2 CH 2 CH 3 ) 2 H 2 C CHCO 2 CH 2 CH 3 CH 3 NH 2 H 2 C 1 O O Methylamine
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Unformatted text preview: Ethyl acrylate (CH 2 ) 4 CH 3 O N H CH 2 CH 2 NH 2 CH 2 CH (CH 2 ) 4 CH 3 O Morpholine 3-Morpholino-1,3-diphenyl-1-propanone (91%) 1,3-Diphenyl-2-propen-1-one HN O C 6 H 5 CCH C 6 H 5 CCH 2 CHC 6 H 5 O O CHC 6 H 5 1 N O HN N O O 1 2-Cyclohexenone Piperidine 3-Piperidinocyclo-hexanone (45%) (CH 3 ) 2 C (CH 3 ) 2 CCH 2 CCH 3 CHCCH 3 NH 3 1 O O NH 2 4-Methyl-3-penten-2-one 4-Amino-4-methyl-2-pentanone (63 70%) Ammonia AMINES 647...
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