[Cl:1][C:2]1[CH:3]=[C:4]([NH:15][C:16](=[O:21])[O:17][CH:18]([CH3:20])[CH3:19])[CH:5]=[C:6]([CH2:12][O:13][CH3:14])[C:7]=1[O:8][CH2:9][C:10]#[N:11].I[CH3:23].[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:23][N:15]([C:4]1[CH:5]=[C:6]([CH2:12][O:13][CH3:14])[C:7]([O:8][CH2:9][C:10]#[N:11])=[C:2]([Cl:1])[CH:3]=1)[C:16](=[O:21])[O:17][CH:18]([CH3:19])[CH3:20]Isopropyl N-(3-chloro-4-cyanomethoxy-5-methoxymethylphenyl)carbamate (3.13 g) and iodomethane (4.30 g) were dissolved in tetrahydrofuran (10 ml). The resultant solution was dropwise added to a tetrahydrofuran solution (20 ml) containing potassium hydroxide (1.68 g) and tetra-n-butylammonium bromide (1.0 g). After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice-water and extracted with toluene. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give isopropyl N-methyl-N-(3-chloro-4-cyanomethoxy-5-methoxymethylphenyl)carbamate (Compound No. 41) (3.06 g) in a yield of 93.5%. nD22.0 1.5123.
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