Hydrogen Peroxide → HCID 87918044, compound

Temperature

0 °C

A 1M solution of BH3 ·THF (11.00 ml, 11.00 mmole) was placed in a 100 ml round-bottom flask equipped with N2 line, dropping funnel and thermometer. The solution was cooled to 0° C. in an ice-water bath. To this cooled solution was added dropwise, (R)-toluene-4-sulfonic acid 8-allyl-7-nitro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester (2.25 g, 5.56 mmole) in 10 ml of dry THF over a 10 minute period. The reaction was allowed to reach room temperature and then stirred overnight. It was then cooled to 0 ° C. and to it was added dropwise 2.42 ml of absolute ethanol and 6.16 ml (18.5 mmole) of a 3N NaOH solution. After a few minutes, 4.2 ml of a 30% aqueous H2O2 solution was added over a 20 minute period. The mixture was heated to 48° C. for three hours. The mixture was then cooled to 0° C. and to it was added 6.08 g of K2CO3. The mixture was stirred for 0.5 hr and then left standing overnight. The following morning the solid had disappeared. The reaction was diluted with water and extracted with ethyl acetate. The organic layer washed with brine, dried over MgSO4, filtered and concentrated to yield a clear viscous oil (1.20 g, 51%) of (R)-toluene-4-sulfonic acid 8-(3-hydroxy-propyl)-7-nitro-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester.

1. additionTo this cooled solution was added dropwise
2. customto reach room temperature
3. temperatureIt was then cooled to 0 ° C. and to it
4. waitAfter a few minutes
5. temperatureThe mixture was heated to 48° C. for three hours
6. temperatureThe mixture was then cooled to 0° C. and to it
7. stirringThe mixture was stirred for 0.5 hr
8. waitleft
9. waitstanding overnight
10. extractionextracted with ethyl acetate
11. washThe organic layer washed with brine
12. dry with materialdried over MgSO4
13. filtrationfiltered
14. concentrationconcentrated

ORD record

ord-74f31087b0ff437aa48a8610389ca7e9

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05756532