3-Butyn-1-OL → HCID 15332557, compound

HRID 1440988Notes

Reaction equation

HRID 1440988 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1I>C(#N)C.C(N(CC)CC)C.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.[Cu]I>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:4]#[C:3][CH2:2][CH2:1][OH:5]

Participants

7

Reactant 2

HCID 135663-Butyn-1-OLHCID 968642,4-Dichloro-1-iodobenzene

Product 1

HCID 15332557HCID 15332557, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Synthesis of an intermediate in which m is 3 is detailed in Example 4. This route starts with the reaction of 3-butyn-1-ol with 2,4-dichloroiodobenzene in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide in acetonitrile and triethylamine, producing 4-(2,4-dichlorophenyl)-3-butyn-1-ol. Hydrogenation of this acetyleneic alcohol over platinum oxide produces 4-(2,4-dichlorophenyl)-1-butanol which is then oxidized with chromium trioxide and sulfuric acid to the corresponding carboxylic acid. The remaining steps are the same as those detailed in Example 1.

Workup

  1. customSynthesis of an intermediate in which m

Sources & evidence

ORD record
ord-6463e9afccca47d3911acf624f7bfff8
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

Loading…