3-Butyn-1-OL → HCID 11605060, compound

HRID 2067295Notes

Reaction equation

HRID 2067295 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:28])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=3)=[CH:14][C:13]=2[Cl:27])=[O:11])[CH:9]=1)=[N+:2]=[N-:3].[CH2:29]([OH:33])[CH2:30][C:31]#[CH:32]>>[Cl:27][C:13]1[CH:14]=[C:15]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH:16]=[CH:17][C:12]=1[C:10]([C:8]1[CH:9]=[C:4]([N:1]2[CH:32]=[C:31]([CH2:30][CH2:29][OH:33])[N:3]=[N:2]2)[CH:5]=[CH:6][C:7]=1[CH3:28])=[O:11]

Participants

3

Reactant 2

HCID 135663-Butyn-1-OLHCID 86605541HCID 86605541, compound

Product 1

HCID 11605060HCID 11605060, compound

Procedure

The reaction was carried out similarly as described in the preparation of compound 116, using compound 468 (0.22 mmol) and but-3-yn-1-ol (0.28 mmol). The crude product was purified by flash chromatography using EtOAc/petroleum ether (40-60) 6:1 as the eluent to afford the title compound as light yellow foam. 13C NMR (CDCl3) δ 194.8, 160.8, 148.5, 141.1, 141.0, 138.1, 135.5, 134.8, 133.9, 132.6, 130.4, 127.8, 122.2, 120.7, 119.9, 116.6, 113.6, 113.2, 109.4, 107.3, 61.6, 55.4, 28.7, 19.9

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6ccdac9192d24ccc983daabbd31668c7
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

Loading…