4-Pentyn-1-ol → HCID 87082527, compound

HRID 341601Notes

Reaction equation

HRID 341601 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.[CH2:19]([OH:24])[CH2:20][CH2:21][C:22]#[CH:23]>>[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:23]#[C:22][CH2:21][CH2:20][CH2:19][OH:24])[CH:3]=1)=[O:17]

Participants

3

Reactant 2

HCID 793464-Pentyn-1-olHCID 57608426N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Product 1

HCID 87082527HCID 87082527, compound

Procedure

Sonogashira reaction of 25 with pent-4-yn-1-ol gave 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(5-hydroxypent-1-ynyl)phenyl)propyl)acetamide as brown oil. Yield (1.46 g, 69%): 1H NMR (400 MHz, CDCl3) δ 7.38 (s, 1H), 7.22-7.34 (m, 3H), 4.86 (d, J=8.0 Hz, 1H), 3.83 (t, J=5.2 Hz, 2H), 3.65-3.69 (m, 1H), 3.38-3.42 (m, 1H), 2.56 (t, J=7.2 Hz, 2H), 2.38 (bs, 1H) 1.93-1.99 (m, 2H), 1.83-1.88 (m, 2H).

Sources & evidence

ORD record
ord-d91a12fdb54d4ae7b95bc6e77cfbf7e0
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

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