4-Ethynylheptan-4-ol → 2,2,2-trifluoro-N-(3-(3-hydroxy-3-propylhex-1-ynyl)phenethyl)-acetamide
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:13])[C:9]([F:12])([F:11])[F:10].[C:17]([C:19]([OH:26])([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])#[CH:18]>>[F:10][C:9]([F:12])([F:11])[C:8]([NH:7][CH2:6][CH2:5][C:4]1[CH:14]=[CH:15][CH:16]=[C:2]([C:18]#[C:17][C:19]([OH:26])([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH:3]=1)=[O:13]Participants
3
Procedure
N-(3-Bromophenethyl)-2,2,2-trifluoroacetamide was coupled with alkynol 20 following the procedure described in Example 18 except that the reaction was run for 17 h to give 2,2,2-trifluoro-N-(3-(3-hydroxy-3-propylhex-1-ynyl)phenethyl)-acetamide as a brown oil after purification by flash chromatography (10% to 50% EtOAc in hexanes gradient). Yield (0.975 g, 66%). 1H NMR (400 MHz, CDCl3) δ 7.32 (dt, J=7.8, 1.2 Hz, 1H), 7.24-7.29 (m, 2H), 7.10-7.15 (m, 1H), 6.27 (br.s, 1H), 3.61 (q, J=6.7 Hz, 2H), 2.86 (t, J=7.0 Hz, 2H), 1.95 (s, 1H), 1.66-1.74 (m, 4H), 1.52-1.64 (m, 4H), 0.99 (t, J=7.2 Hz, 6H).
Sources & evidence
- ORD record
- ord-bee291cf27ab4880a784f70dc1e1023f
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895782B2
Reaction notes
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