3-Methyl-1-hexyn-3-ol → 2,2,2-Trifluoro-n-(3-hydroxy-3-(3-(3-hydroxy-3-methylhex-1-ynyl)phenyl)propyl)acetamide

HRID 454404Notes

Reaction equation

HRID 454404 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.[CH3:19][C:20]([OH:26])([CH2:23][CH2:24][CH3:25])[C:21]#[CH:22]>>[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:22]#[C:21][C:20]([OH:26])([CH3:19])[CH2:23][CH2:24][CH3:25])[CH:3]=1)=[O:17]

Participants

3

Reactant 2

HCID 203473-Methyl-1-hexyn-3-olHCID 57608426N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Product 1

HCID 870824992,2,2-Trifluoro-n-(3-hydroxy-3-(3-(3-hydroxy-3-methylhex-1-ynyl)phenyl)propyl)acetamide

Procedure

Sonogashira reaction of 25 with 3-methylhex-1-yn-3-ol yielded 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(3-hydroxy-3-methylhex-1-ynyl)phenyl) propyl)acetamide as dark brown oil. Yield (0.611 g, 55%): 1H NMR (400 MHz, CDCl3) δ 7.41 (s, 1H), 7.24-7.37 (m, 3H), 4.86 (m, 1H), 3.67-3.72 (m, 1H), 3.38-3.44 (m, 1H), 2.32 (bs, 1H), 1.94-2.01 (m, 3H), 1.71-1.76 (m, 2H), 1.59-1.62 (m, 1H), 1.53 (s, 3H), 0.99 (t, J=7.2, 3H).

Sources & evidence

ORD record
ord-46393f301dc6425e8bd75e49d27668ad
Source dataset
uspto-grants-2013_07
Patent number
US08492589B2

Reaction notes

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