Oxygen → HCID 11242347, compound

An aqueous NH4Cl solution was saturated at 5° C. CuCl (1.0 g, 18.7 mmol) was added to 20 ml of the saturated aqueous NH4Cl solution. The reaction vessel was filled with O2 and the mixture was vigorously stirred during the whole reaction time. 3-(2-propynyloxy)-propane-1,2-diol (4, 13.01 g, 100 mmol) was added at room temperature in 5 portions during 2.5 hours. The reaction mixture was stirred at 40° for 1 hour and then evaporated to dryness. The residue was dissolved in 50 ml CH3CN:H2O=1:1 and filtered through 20 g silica 60. The filter column was washed with 100 ml CH3CN:H2O=1:1 and the filtrate was evaporated to dryness. The residue was suspended in MeOH (70 ml) and insoluble inorganic components removed by filtration. The filtrate was diluted with water (500 ml) and stirred with ion exchangers (IRA 67, 110 ml; AMB 200 C, 110 ml) and activated carbon (0.1 g). The ion exchangers were filtered off and washed with water (2×250 ml). The combined filtrates were evaporated and gave 9.8 g 17 as a light yellow oil in 76% yield. TLC on silica; H2O:CH3CN=1:1, Rf=0.79; CH3CN, Rf=0.26.

1. customwas saturated at 5° C
2. stirringThe reaction mixture was stirred at 40° for 1 hour
3. customevaporated to dryness
4. dissolutionThe residue was dissolved in 50 ml CH3CN
5. filtrationH2O=1:1 and filtered through 20 g silica 60
6. washThe filter column was washed with 100 ml CH3CN
7. customH2O=1:1 and the filtrate was evaporated to dryness
8. custominsoluble inorganic components removed by filtration
9. additionThe filtrate was diluted with water (500 ml)
10. stirringstirred with ion exchangers (IRA 67, 110 ml; AMB 200 C, 110 ml) and activated carbon (0.1 g)
11. filtrationThe ion exchangers were filtered off
12. washwashed with water (2×250 ml)
13. customThe combined filtrates were evaporated

ORD record

ord-00d8694ee7344c959c34df36e8dca4a8

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06406680B1