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

HRID 2070649Notes

Reaction equation

HRID 2070649 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:18])[CH2:9][CH2:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:5]=[CH:6][CH:7]=1.[CH:19]#[C:20][CH:21]([OH:25])[CH2:22][CH2:23][CH3:24]>>[F:14][C:13]([F:16])([F:15])[C:12]([NH:11][CH2:10][CH2:9][CH:8]([OH:18])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:19]#[C:20][CH:21]([OH:25])[CH2:22][CH2:23][CH3:24])[CH:3]=1)=[O:17]

Participants

3

Reactant 2

HCID 7746PropylethinylcarbinolHCID 57608426N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Product 1

HCID 866284552,2,2-trifluoro-N-(3-hydroxy-3-(3-(3-hydroxyhex-1-ynyl)phenyl)propyl)acetamide

Procedure

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).

Sources & evidence

ORD record
ord-728f679ff3294f5fb5395cf7625bfd9d
Source dataset
uspto-grants-2012_10
Patent number
US08299307B2

Reaction notes

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