Chloride → 63880-78-4

Temperature

-80 °C

13 mL of DMSO (246 mmol) was gradually added to a solution prepared by dissolving oxaryl chloride (5.8 mL, 66 mmol) in 123 mL of CHCl3, which solution had been cooled to −80° C., and the mixture was stirred for three minutes. 6.8 g of 4-allyloxy-1-butanol (52 mmol) was then added to the mixture. After the solution was stirred for 15 minutes, 43 mL of triethylamine (594 mmol) was added thereto and the reaction solution was stirred for 10 hours, while the temperature of the reaction solution was allowed to return to room temperature. The reaction was quenched by adding distilled water and the CHCl3 layer was separated. The separated layer was washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine and dried with anhydrous Na2SO4. The solvent was distilled away under reduced pressure, whereby pale yellow liquid was obtained (6.0 g, 90%).

1. customprepared
2. stirringAfter the solution was stirred for 15 minutes
3. stirringthe reaction solution was stirred for 10 hours, while the temperature of the reaction solution
4. customto return to room temperature
5. customThe reaction was quenched
6. additionby adding
7. distillationdistilled water
8. customthe CHCl3 layer was separated
9. washThe separated layer was washed with diluted hydrochloric acid, saturated aqueous sodium bicarbonate and saturated brine
10. dry with materialdried with anhydrous Na2SO4
11. distillationThe solvent was distilled away under reduced pressure, whereby pale yellow liquid
12. customwas obtained (6.0 g, 90%)

ORD record

ord-27d938db11a049ddaf5a0e798a700efb

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192650B2