Propylethinylcarbinol → 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(3-hydroxyhex-1-ynyl)phenyl)propyl)acetamide

Participants

Role	Name	HCID	Charge
Reactant	Propylethinylcarbinol	HCID 7746	—
Reactant	N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide	HCID 57608426	—
Product	2,2,2-trifluoro-N-(3-hydroxy-3-(3-(3-hydroxyhex-1-ynyl)phenyl)propyl)acetamide	HCID 86628455	—

Reaction Steps

Sonogashira reaction of 25 (3 g, 9.2 mmol) with hex-1-yn-3-ol yielded 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(3-hydroxyhex-1-ynyl)phenyl) propyl)acetamide as yellow oil. Yield (2.31 g, 73%): 1H NMR (400 MHz, CDCl3) δ 7.42 (s, 1H), 7.26-7.38 (m, 3H), 4.86 (m, 1H), 4.61 (dd, J=2.0, 5.6 Hz, 1H), 3.67-3.71 (m, 1H), 3.37-3.46 (m, 1H), 2.38 (d, J=2.0 Hz, 1H), 1.95-1.99 (m, 2H), 1.75-1.88 (m, 2H), 1.53-1.57 (m, 2H), 0.97 (t, J=7.2 Hz, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08492589B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-6a2258061ad34c2097f7c48c25aa5e68
Source note	uspto-grants-2013_07