Triethylamine → Hydroxyphenylacetylene

HRID 365978Notes

Reaction equation

HRID 365978 reaction equation
C[C@H](NCCC1C=CC(O)=CC=1)[C@H](O)C1C=C[C:7]([OH:10])=[CH:6]C=1.C[Si]([C:26]#[CH:27])(C)C.[SiH3][C:29]#[CH:30].[CH2:31](N(CC)CC)[CH3:32]>[Pd]>[OH:10][C:7]#[C:6][C:27]1[CH:26]=[CH:30][CH:29]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 33572RitodrineHCID 66111TrimethylsilylacetyleneHCID 136821Monosilylacetylene

Product 1

HCID 10909551HydroxyphenylacetyleneYield 60%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In recent year, Polymer. Prepar. 1993, 34(1), 511-12. and Japanese Laid Open Patent HEI 8-217698 have described a process that 3- or 4-halophenol having a protected hydroxyl group, when necessary, is subjected to coupling with trimethylsilylacetylene or other monosilylacetylene in a triethylamine solvent in the presence of a palladium catalyst and thereafter subjected to removing of the silyl group and where necessary, deprotecting of the hydroxyl group to obtain desired hydroxyphenylacetylene in a considerably high yield of 60 to 80%.

Workup

  1. customto removing of the silyl group and where necessary

Sources & evidence

ORD record
ord-62a95325c1e345c7bede9dc12f967120
Source dataset
uspto-grants-2000_10
Patent number
US06127583

Reaction notes

Loading…