Stobbe condensations of dimethyl 3,5-bis(benzyloxy)homophthalate

Abstract

DIMBTHYL 3,5-Bis (benzyloxy)homophthalate(2:1), to give 0.35 g (72%) of a homogeneous foam. This was identified with compound 20 obtained above by nmr and uv spectroscopy.

Synthesis of 3-alkyl-2-benzamido-4-hydroxy-2-butenoic acid .gamma.-lactones from alkyl cuprates. Attempted transformation to 2,3-diaminocarboxylic acids by hydrogenation and Curtius rearrangement

“…jV-Benzoyl-3-bromo-2,3-didehydrohomoserine 7-Lactone (8). To a stirred solution of 4.06 g (20 mmol) of 7 in 50 mL of dry dichloromethane was added dropwise over a period of 30 min 20 mL of 1.0 M bromine in dichloromethane.…”

“…The cooled flask was then charged with 10 mL of dry THF, 0.25 mL of purified boron trifluoride etherate (2 mmol), and 1.7 mL of 1.2 M methyllithium in ether (2 mmol), and the mixture was stirred for 10 min. A solution of 0.28 g (1 mmol) of JV-benzoyl-3-bromo-2,3-didehydrohomoserine 7-lactone (8) in 8 mL of dry THF was added, and the solution was stirred for 30 min. The dropping funnel was then charged with a solution of 3 mmol of lithium dimethylcuprate in THF-ether [prepared from cuprous iodide (0.28 g, 3 mmol), THF (7 mL), and methyllithium (2.5 mL of a 1.2 M solution in ether)].…”

“…

The reaction of lithium dialkylcuprate reagents with 2-benzamido-3-bromo-4-hydroxybut-2-enoic acid 7-lactone (8) gave the corresponding 3-alkylbut-2-enoic acid 7-lactone derivatives 3. With lithium dimethylcuprate, a low yield of product was obtained; however, use of a new combined cuprate reagent, (CHg^CuLi-CK^Li-BF^, provided 3-methylbut-2-enoic acid 7-lactone (10) in good yield.

…”

“…Chem. 1978, 43, 3713. Scheme IIa Bromination of 7 and subsequent elimination11,16 furnished the required iV-benzoyl-3-bromo-2,3-didehydrohomoserine 7-lactone (8).…”

Green Synthesis of Acid Esters from Furfural via Stobbe Condensation

“…Fulgides are important for their photochromic properties [1][2][3]. Stobbe condensation [4][5][6][7][8][9][10], a C-C bond forming reaction, is a pathway to fulgides. A lot of research has been done on photochromic fulgides; among them, furan ring containing fulgides [11] have maintained the interest of researchers through decades of development of organic synthesis.…”