[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14]O)=[CH:8][CH:7]=1.C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N-:36]=[N+:37]=[N-:38].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CN(C=O)C>[N:36]([CH2:14][CH2:13][C:12]([C:9]1[CH:10]=[CH:11][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][CH:8]=1)([CH3:17])[CH3:16])=[N+:37]=[N-:38]
To a cooled solution (0° C.) of 3-(4-furan-2-yl-phenyl)-3-methyl-butan-1-ol (1.2 g, 5.2 mmol) (reference example 22) in CH2Cl2 (17 mL) is added triethylamine (0.86 mL, 6.2 mmol), p-toluenesulfonyl chloride (1.18 g, 6.2 mmol) and 4-dimethylaminopyridine (305 mg, 2.5 mmol). The resulting solution is allowed to warm to 20° C. while stirring for 1.5 h then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is dissolved if DMF (17 mL), sodium azide (845 mg, 13 mmol) added and the mixture heated to 60° C. and stirred for 3 h. The mixture is cooled to 20° C., then diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 10% ethyl acetate in hexanes) to give 1.06 g of title compound as a colorless oil. 1H NMR (CDCl3) δ 1.36 (s, 6H), 1.95 (t, J=8 Hz, 2H), 3.03 (t, J=8 Hz, 2H), 6.46 (m, 1H), 6.62 (m, 1H), 7.34 (d, J=8 Hz, 2H), 7.46 (d, J=2 Hz, 1H), 7.62 (d, J=8 Hz, 2H). MS (ion spray) m/z 256 (M+H)+.
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