3-METHOXY-5-METHYLBENZALDEHYDE

To a mixture of D-4-1 (200 g, 0.995 mol) in dry THF (1.7 L), at −70° C., is added drop wise a solution of n-BuLi in hexanes (438 ml; 1.09 mol). After stirring for 1 h at −70° C., dry DMF (76.3 g, 1.04 mol) is added drop wise at −70° C. Following this, the mixture is stirred for 1 h at −70° C. The mixture is poured into NHTo a mixture of 25-02 (200 g, 0.995 mol) in dry THF (1.70 L) is added dropwise n-BuLi (438 ml; 1.09 mol) at -70° C. General procedure: To a solution of the hydroxy-methylbenzaldehyde (34 mg, 0.25 mmol) in anhydrous DMF (6.0 mL), K2CO3 (35 mg, 0.25 mmol) was added and the mixture was stirred at room temperaturefor 30 minutes. Then, methyl iodide (30 μL, 68 mg, 0.5 mmol) was added and the reaction was stirred at room temperatureovernight. The reaction was quenched by the additionof distilled water, and the aqueous phase was extracted threetimes with ethyl acetate. The combined organic phases weredried with MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel.B) General procedure: To a solution of the hydroxy-methylbenzaldehyde (34 mg, 0.25 mmol) in anhydrous DMF (6.0 mL), K2CO3 (35 mg, 0.25 mmol) was added and the mixture was stirred at room temperaturefor 30 minutes. Then, methyl iodide (30 muL, 68 mg, 0.5 mmol) was added and the reaction was stirred at room temperatureovernight. The reaction was quenched by the additionof distilled water, and the aqueous phase was extracted threetimes with ethyl acetate. The combined organic phases weredried with MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel.N, N, N?-trimethylethylenediamine (3.80 g, 37.2 mmol) and tetrahydrofuran (10 mL) were added to a 250 mL two-neck flask, and n-butyllithium (16 mL, 38.4 mmol, 2.4 M in THF) was added dropwise at -65C. The mixture was stirred for 0.5 h at -65C. A solution of B)

Molecular Weight:150.17
XLogP3:1.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:150.068079557
Monoisotopic Mass:150.068079557
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes