2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide → 2,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)prop-2-ynyl)acetamide

HRID 517157Notes

Reaction equation

HRID 517157 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]([OH:17])([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:5]=[CH:6][CH:7]=1.[F:18][C:19]([F:27])([F:26])[C:20]([NH:22][CH2:23][C:24]#[CH:25])=[O:21]>>[F:18][C:19]([F:27])([F:26])[C:20]([NH:22][CH2:23][C:24]#[C:25][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][C:10]([OH:17])([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:3]=1)=[O:21]

Participants

3

Reactant 2

HCID 110948052,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamideHCID 66629554HCID 66629554, compound

Product 1

HCID 866284702,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)prop-2-ynyl)acetamide

Procedure

4-((3-bromophenyl)ethynyl)heptan-4-ol was coupled with 2,2,2-trifluoro-N-(prop-2-ynyl)acetamide following the procedure described in Example 10 to give 2,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)prop-2-ynyl)acetamide as a pale yellow oil. Yield (0.083 g, 6%): 1H NMR (400 MHz, DMSO-d6) δ 10.03 (t, J=5.2 Hz, 1H), 7.40-7.33 (m, 4H), 5.16 (bs, 1H), 4.25 (d, J=5.6 Hz, 2H), 1.61-1.39 (m, 8H), 0.89 (t, J=7.2 Hz, 6H).

Sources & evidence

ORD record
ord-401e826b812d41058a7d7a15d32828d1
Source dataset
uspto-grants-2015_08
Patent number
US09115056B2

Reaction notes

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