Phenylacetylene → Tert-butyl 3-hydroxy-3-(3-(phenylethynyl)phenyl)propylcarbamate

HRID 658847Notes

Reaction equation

HRID 658847 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:19])[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.[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[CH:21]>>[OH:19][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:21]#[C:20][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:3]=1)[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 57608439Tert-butyl 3-(3-bromophenyl)-3-hydroxypropylcarbamate

Product 1

HCID 66742835Tert-butyl 3-hydroxy-3-(3-(phenylethynyl)phenyl)propylcarbamate

Procedure

Sonogashira reaction of 39 with ethynylbenzene gave tert-butyl 3-hydroxy-3-(3-(phenylethynyl)phenyl)propylcarbamate as brown oil. Yield (0.911 g, 85%): 1H NMR (400 MHz, CDCl3) δ 7.51-7.55 (m, 3H), 7.42-7.44 (m, 1H), 7.30-7.37 (m, 5H), 4.87 (bs, 1H), 4.74-4.76 (m, 1H), 3.46-3.51 (m, 1H), 3.41 (bs, 1H), 3.13-3.19 (m, 1H), 1.79-1.88 (m, 2H), 1.44 (s, 9H).

Sources & evidence

ORD record
ord-fadbb68bd454466fa5ddcee6b969b9d3
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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