Iodine → HCID 86750693、化合物

温度

0 °C

To a suspension of benzenesulphinic acid sodium salt (7.59 g, 46.2 mmol) and tert-butyl 2-(2-methoxyethoxymethyl)acrylate (10.0 g, 46.2 mmol) in ethyl acetate (50 mL) under a nitrogen atmosphere at room temperature was added, in one portion, iodine (11.3 g, 46.2 mmol) and the mixture stirred for 3 days. An additional 50 mL of ethyl acetate was added after 2 days. The reaction mixture was cooled to 0° C. and triethylamine (9.67 mL, 69.3 mmol) added dropwise. The reaction was stirred at 0° C. for 2 hours and at room temperature for 16 hours and diluted with distilled water (100 mL) and ethyl acetate (50 mL). The layers were separated and the aqueous layer further extracted with ethyl acetate (25 mL). The combined ethyl acetate extracts were washed with a 1.0M aqueous hydrochloric acid solution and 5% aqueous sodium thiosulphate solution (2×100 mL), filtered to remove solids and the filter pad washed with ethyl acetate. The combined filtrate and washings were washed with distilled water (50 mL), and concentrated under reduced pressure to give a brown oil, (14.85 g). The crude product was purified by chromatography on silica by eluting with hexane/ethyl acetate (2:1) to give, after combination and evaporation of appropriate fractions, the title compound as an oil, (5.09 g, 30.8%) which crystallised on standing, m.pt.=46°-48° C., Rf =0.25 (silica, hexane/ethyl acetate, 2:1), (MH+ 357.05, 1.7%).

1. stirringThe reaction was stirred at 0° C. for 2 hours and at room temperature for 16 hours
2. customThe layers were separated
3. extractionthe aqueous layer further extracted with ethyl acetate (25 mL)
4. washThe combined ethyl acetate extracts were washed with a 1.0M aqueous hydrochloric acid solution and 5% aqueous sodium thiosulphate solution (2×100 mL)
5. filtrationfiltered
6. customto remove solids
7. washthe filter pad washed with ethyl acetate
8. washThe combined filtrate and washings were washed with distilled water (50 mL)
9. concentrationconcentrated under reduced pressure
10. customto give a brown oil, (14.85 g)
11. customThe crude product was purified by chromatography on silica
12. washby eluting with hexane/ethyl acetate (2:1)
13. customto give
14. customafter combination and evaporation of appropriate fractions
15. customthe title compound as an oil, (5.09 g, 30.8%) which crystallised

ORDレコード

ord-f3c471e384064f06b77747e5908f7cd1

出典データセット

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05618970