4-Pentyn-1-ol → Tert-butyl 3-(3-(5-hydroxypent-1-ynyl)phenyl)propylcarbamate

HRID 2098508Notes

Reaction equation

HRID 2098508 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.[CH2:19]([OH:24])[CH2:20][CH2:21][C:22]#[CH:23]>>[OH:24][CH2:19][CH2:20][CH2:21][C:22]#[C:23][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 793464-Pentyn-1-olHCID 57219374Tert-butyl 3-(3-bromophenyl)propylcarbamate

Product 1

HCID 66742928Tert-butyl 3-(3-(5-hydroxypent-1-ynyl)phenyl)propylcarbamate

Procedure

Sonogashira reaction of bromide 57 with 4-pentyn-1-ol gave tert-butyl 3-(3-(5-hydroxypent-1-ynyl)phenyl)propylcarbamate as yellow oil. Yield (0.653 g, 59%): 1H NMR (400 MHz, CDCl3) δ 7.17-7.23 (m, 3H), 7.08 (d, J=7.2 Hz, 1H), 4.53 (bs, 1H), 3.83 (t, J=6.0 Hz, 2H), 3.10-3.18 (m, 2H), 2.60 (t, J=7.8 Hz, 2H), 2.54 (t, J=7.0 Hz, 2H), 1.83-1.90 (m, 2H), 1.74-1.82 (m, 2H), 1.44 (s, 9H).

Sources & evidence

ORD record
ord-d82de0c2894d4f1f944c511763204cd8
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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