4-Ethynylheptan-4-ol → HCID 86628471, compound

HRID 341622Notes

Reaction equation

HRID 341622 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][NH:6][C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].[C:16]([C:18]([OH:25])([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])#[CH:17]>>[F:9][C:8]([F:11])([F:10])[C:7]([NH:6][CH2:5][C:4]1[CH:13]=[CH:14][CH:15]=[C:2]([C:17]#[C:16][C:18]([OH:25])([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])[CH:3]=1)=[O:12]

Participants

3

Reactant 2

HCID 123838984-Ethynylheptan-4-olHCID 55138583HCID 55138583, compound

Product 1

HCID 86628471HCID 86628471, compound

Procedure

N-(3-bromobenzyl)-2,2,2-trifluoroacetamide was coupled with alkynol 20 following the procedure described in Example 10 to give 2,2,2-trifluoro-N-(3-(3-hydroxy-3-propylhex-1-ynyl)benzyl)acetamide as a yellow oil. Yield (0.462 g, 38%): 1H NMR (400 MHz, DMSO-d6) δ 9.97 (t, J=5.6 Hz, 1H), 7.32 (t, J=7.8 Hz, 1H), 7.27-7.22 (m, 3H), 5.15 (bs, 1H), 4.35 (d, J=6.0 Hz, 2H), 1.60-1.41 (m, 8H), 0.89 (t, J=7.2 Hz, 6H).

Sources & evidence

ORD record
ord-286313b7146f48b7a0131f256f583323
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

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