Sodium hydride → HCID 22638837、化合物

Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate (6.13 g, 25.6 mmol) was added dropwise via syringe to a stirred suspension of sodium hydride (1.02 g, 25.6 mmol) in anhydrous THF (75 ml) at 0° C. The reaction was warmed to room temperature and was stirred for 1 h. After cooling to 0° C., benzo[b]thiophene-3-carbaldehyde (3.78 g, 23.3 mmol) was added. The resulting mixture was stirred at room temperature for 1 hr. The reaction was quenched with 100 mL aqueous HCl (0.1 N) and extracted with ethyl acetate (250 ml). The combined organic layers were washed with brine (50 ml) and dried over anhydrous magnesium sulfate. The filtrate was concentrated in vacuo and triturated with hexane to give (E)-3-benzo[b]thiophen-3-yl-N-methoxy-N-methyl-acrylamide (5.38 g, 93%) as a yellow solid. 1H NMR (500 MHz, CDCl3) 8.06-8.01 (2H, 2 superimposed d, J=8.24, 15.87 Hz), 7.89 (1H, d, J=7.94 Hz), 7.78 (1H, s), 7.47 (1H, t, J=7.93 Hz), 7.41 (1H, t, J=8.24 Hz), 7.13 (1H, d, J=15.87 Hz), 3.79 (3H, s), 3.34 (3H, s); MS m/e 248.07 (M+H)+.

1. temperatureAfter cooling to 0° C.
2. stirringThe resulting mixture was stirred at room temperature for 1 hr
3. customThe reaction was quenched with 100 mL aqueous HCl (0.1 N)
4. extractionextracted with ethyl acetate (250 ml)
5. washThe combined organic layers were washed with brine (50 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationThe filtrate was concentrated in vacuo
8. customtriturated with hexane

ORDレコード

ord-090caecb407a4a1b9194ab951b99cd35

出典データセット

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06777437B2