Methyl trifluoroacetate → 8-Trifluoroacetamido-3,6-dioxa-1-octanol
Reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10].[F:11][C:12]([F:17])([F:16])[C:13](N)=[O:14].FC(F)(F)C(OC)=O>>[F:11][C:12]([F:17])([F:16])[C:13]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][OH:10])=[O:14]Participants
4
Procedure
The amino group of 2-(2-(2-aminoethoxy)ethoxy)ethanol was protected as the trifluoroacetamide by reaction with excess of methyl trifluoroacetate to give in 98% yield. Briefly, methyl trifluoroacetate (3.20 g, 2.52 ml, 25 mmol) was added dropwise through a septum with stirring and gentle cooling to 2-(2-(2-aminoethoxy)ethoxy)ethanol (2.98 g, 20 mmol), and the mixture was sealed and left at room temperature for 24 hours. The volatiles were evaporated under membrane pump vacuum and bath temperature of 65° C. to give trifluoro-N-(2-(2-(2-hydroxyethoxy)ethoxy)ethyl)acetamide as a slightly yellowish oil which crystallized when stored in the refrigerator: 4.83 g, 98% yield. 1H NMR (DMSO-d6): δ 9.41 (t, 1H, NH), 4.57 (bs, 1H, OH), 3.55-3.28 (m, 12H, CH2); 13C NMR (DMSO-d6): δ 156.60 (q, J=36.1 Hz, CO), 115.96 (q, J=116 Hz, CF3), 73.15, 70.50, 70.46, 68.67, 61.08, 39.99.