1-Pentyne → Ethyl (3-(pentyne-1-yl)phenyl)acetate

HRID 475544Notes

Reaction equation

HRID 475544 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:14]#[C:15][CH2:16][CH2:17][CH3:18].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:14]([C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1)#[C:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 123091-PentyneHCID 11470552Ethyl 3-(bromophenyl)acetateHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrate

Product 1

HCID 67100180Ethyl (3-(pentyne-1-yl)phenyl)acetate

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

heating a mixture of ethyl [3-bromophenyl]acetate and 1-pentyne in the presence of tetrabutylammonium fluoride hydrate and PdCl2(PPh3)2 to provide ethyl [3-[pentyne-1-yl]phenyl]acetate;

Workup

  1. temperatureheating

Sources & evidence

ORD record
ord-53b4b91e002c4269bcde73d56d1c0292
Source dataset
uspto-grants-2014_01
Patent number
US08637574B2

Reaction notes

Loading…