Sodium Bicarbonate → HCID 71268277, compound

Participants

Reaction Steps

1,4-Oxazepane hydrochloride (1.6 g) and acetic acid (0.90 mL) were added to a chloroform (20 mL) solution of ethyl 4-[(4-formylphenyl)ethynyl]benzoate (2.1 g) as obtained in Example 5-(1), and the mixture was stirred for 3.5 hours at room temperature, and then for 2 hours at 60° C. Then, sodium triacetoxyborohydride (2.7 g) was added, and the mixture was stirred for 16 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with brine, and dried over anhydrous sodium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by OH type silica gel chromatography (gradient elution with chloroform/methanol=100/0→93/7) to obtain ethyl 4-{[4-(1,4-oxazepan-4-ylmethyl)phenyl]ethynyl}benzoate (yellow solid) (1.5 g, 52%).

Provenance & Evidence