methyl 12-oxododecanoate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 12-Oxo-dodecanoic acid methyl ester (14.5 g, 63.4 mmol) and (5-tert-butoxycarbonyl-thiophen-2-ylmethyl)-triphenylphosphonium bromide (29.1 g, 63.4 mmol) were dissolved in DMF (350 mL). DBU was added and the mixture was heated to 80° C. for 35 minutes. The reaction mixture was allowed to cool to room temperature and separated between diethyl ether (3×500 mL) and water (2000 mL). The organic phases were collected and washed with water (1×500 mL). The organic phase was dried (MgSO4) and the solvent was removed in vacuo. The remaining crude material was added heptane (300 mL) and stirred for 30 minutes, filtered and the solvent was removed in vacuo to yield 13.6 g of crude material of an E/Z mixture of 5-(12-methoxycarbonyl-dodec-1-enyl)thiophene-2-carboxylic acid tert-butyl ester. This mixture was dissolved in methanol (200 mL). 2 g of 10% Palladium on carbon (50% wet with water) was added and the mixture was stirred under a hydrogen atmosphere with 10 bar pressure for 90 minutes, filtered and the solvent was removed in vacuo to yield 11.6 g of 5-(12-methoxycarbonyl-dodecyl)-thiophene-2-carboxylic acid tert-butyl ester. to cool to room temperature separated between diethyl ether (3×500 mL) and water (2000 mL) The organic phases were collected washed with water (1×500 mL) The organic phase was dried (MgSO4) the solvent was removed in vacuo The remaining crude material was added heptane (300 mL) filtered the solvent was removed in vacuo to yield the mixture was stirred under a hydrogen atmosphere with 10 bar pressure for 90 minutes filtered the solvent was removed in vacuo