Sodium Hydroxide → HCID 10784136, compound

Participants

Reaction Steps

A suspension of aluminum chloride (1.76 g, 12.8 mmol) in CH2Cl2 (25 mL) is stirred at room temperature for 15 min and the compound of Example 1 (2.07 g, 6.38 mmol) in CH2Cl2 (15 mL) is added at 5° C. and the resulting mixture is stirred 10 min and cooled to 0° C. A solution of dichloromethyl methyl ether (1.52 g, 17.4 mmol) in 10 mL of CH2Cl2 is added dropwise over a period of 15 min. The mixture is allowed to warm to ambient temperature, stirred overnight and then diluted with of 2N HCl (10 mL) and cool water (100 mL). The mixture is poured into CHCl3 (100 mL), basified with 2N NaOH solution to pH 8-9 and the layers are separated. The aqueous layer is extracted with CHCl3 (40 mL). The combined organic layers are washed with water and dried over Na2SO4. Concentration and drying in vacuo gives crude aldehyde (2.16 g, 96%) which can be used without additional purification. The analytical sample is obtained by silica gel chromatography (EtOAc) following by recrystallization from EtOAc/hexane (1:2), mp: 81°-82.5° C. 1H NMR (CDCl3) 0.95 (6H; t), 2.54 (4H; q), 2.95 (2H; t), 4.40 (2H; t), 7.02 (1H; d), 7.23-7.40 (2H; m), 7.51-7.54 (1H; m), 7.64 (1H; d), 8.17-8.20 (1H; m), 10.02 (1H; s)ppm. MS m/z 352 (MH+). Anal. (C20H21N3OS) C, H, N.

Provenance & Evidence