N#N.[CH3:3][O:4][CH2:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.CN(C)CCN(C)C.[Li]CCCC.CN([CH:27]=[O:28])C.[NH4+].[Cl-]>C1COCC1.CCCCCCC>[CH3:3][O:4][CH2:5][C:6]1[S:7][C:8]([CH:27]=[O:28])=[CH:9][CH:10]=1In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(methoxymethyl)thiophene (1.23 g, 9.58 mmol) in THF (50.0 mL) was treated dropwise at −75° C. with N,N,N′,N′-tetramethyl-ethylendiamin (2.69 ml, 17.7 mmol) followed by n-BuLi (6.5 mL of a 2.7 M solution in heptane, 17.7 mmol). The resulting mixture was stirred for 90 min at −70° C. DMF (4.03 mL, 52.1 mmol) was then added and the resulting mixture was allowed to gently warm-up to rt. The mixture was then poured over sat. aq. NH4Cl (40 mL) and the org. layer was extracted with EA (3×20 mL) and the combined org. layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (gradient from 95:5 hept-EA to 85:15 hept-EA) gave the title compound as an orange oil. LC-MS-conditions 07: tR=0.62 min.
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