C[O-].[Na+].[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][CH:14]=[O:15])=[CH:7][C:6]=1[O:16][CH3:17].[CH2:18](OS(C1C=CC(C)=CC=1)(=O)=O)[C:19]#[C:20][CH2:21][CH3:22]>CO>[CH3:17][O:16][C:6]1[CH:7]=[C:8]([CH2:11][CH2:12][NH:13][CH:14]=[O:15])[CH:9]=[CH:10][C:5]=1[O:4][CH2:18][C:19]#[C:20][CH2:21][CH3:22]41 ml NaOMe 30% in methanol are added to a solution of 31.5 g (180 mmol) N-[2-(4-hydroxy-3-methoxy-phenyl)-ethyl]-formamide in 880 ml methanol. 48.1 g (184 mmol) toluene-4-sulfonic acid pent-2-ynyl ester are added and the mixture is refluxed for 4 hours. After evaporation the residue is taken up in ethyl acetate and washed with water. After evaporation the residue is submitted to flash-chromatography and crystallisation in ether to give 27.8 g (61%) of the N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-formamide. 1H-NMR (300 MHz, CDCl3): 1.14 (t, 3 H, CH2CH3), 2.22 (m, 2 H, CH2CH3), 2.81 (t, 2 H, CH2CH2), 3.48 and 3.57 (2 q (17:83), 2 H, CH2CH2), 3.88 (s, 3 H, OCH3), 4.70 (m, 2 H, OCH2), 5.58 (b, 1 H, NH), 6.73 (m, 2 H, arom.), 6.98 (m, 1 H, arom.), 8.14 (s, 1 H, CHO).
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