Thiourea → Di-tert-butyl (3-fluoro-4-formylphenyl)(methyl)malonate
Reaction equation
[C:1]([O:5][C:6](=[O:28])[C:7]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2OCC[O:23]2)=[C:18]([F:27])[CH:17]=1)([CH3:15])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].NC(N)=S>CCO.O>[F:27][C:18]1[CH:17]=[C:16]([C:7]([CH3:15])([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:28])[CH:21]=[CH:20][C:19]=1[CH:22]=[O:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Di-tert-butyl[4-(1,3-dioxolan-2-yl)-3-fluorophenyl](methyl)malonate (0.91 g, 2.30 mmol) and thiourea (0.87 g, 11.4 mmol) were stirred in refluxing EtOH/H2O (6.7 mL/6.7 mL) for 7 hours. Room temperature was attained and the solvent removed in vacuo. H2O (100 mL) was added to the residue and the products extracted into EtOAc (2×100 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to give the clean product (pale yellow gum). 1H NMR (CDCl3) δ 10.33 (s, 1H), 7.82 (t, J=8.1 Hz, 1H), 7.31 (dd, J=8.1, 1.8 Hz. 1H). 7.27 (dd, J=12.0, 1.8 Hz, 1H), 1.77 (s, 3H), 1.46 (s, 18H).