Water → Dichloromethane isopropanol ammonium hydroxide

The alcohol (30.0 grams) from Example 3 and 7.2 grams of 1,1'-carbonyldiimidazole were dissolved in 300 mL of anhydrous dichloromethane under nitrogen. The reaction was stirred for 16 hours at room temperature and then diluted is with 1 L of dichloromethane. Water (1 L) was added and the mixture was stirred vigorously for ten minutes. The phases were separated and the organic phase was washed twice with is water, dried over anhydrous sodium sulfate and filtered. Ethylenediamine (7.33 mi) was added and the reaction was allowed to stir for 16 hours under nitrogen. The organic phase was washed three times with water, once with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo to give an oil. The oil was chromatographed on silica gel, eluting first with dichloromethane and then with dichloromethane/ isopropanol/ammonium hydroxide (9:0.9:0.1) to yield 6.0 grams of the desired product as a yellow oil. The product had an average of 22 ethoxyethylene units. 1H NMR (CDC3) δ 7.05-7.25 (m, 2H), 6.7-6.9 (m, 2H), 4.15-4.25 (bt, 2H), 4.05-4.15 (bt, 2H), 3.2-4.0 (m, 71H), 2.8-3.0 (bt, 2H), 0.6-2.0 (m, 140H).

1. additiondiluted
2. stirringthe mixture was stirred vigorously for ten minutes
3. customThe phases were separated
4. washthe organic phase was washed twice
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. additionEthylenediamine (7.33 mi) was added
8. stirringto stir for 16 hours under nitrogen
9. washThe organic phase was washed three times with water
10. dry with materialonce with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate
11. filtrationfiltered
12. customthe solvent removed in vacuo
13. customto give an oil
14. customThe oil was chromatographed on silica gel
15. washeluting first with dichloromethane

ORD record

ord-fdff1c08f530421e88c7f4fc836d4feb

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05306314