Methyl trifluoroacetate → 8-Trifluoroacetamido-3,6-dioxa-1-octanol

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.

1. customto give in 98% yield
2. customthe mixture was sealed
3. customThe volatiles were evaporated under membrane pump vacuum and bath temperature of 65° C.

ORD record

ord-e3c7d94e7f5b42db99e2c41c28a1dc6c

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084589B2