(4-Ethynyl-2-methyl-phenyl)-methanol → HCID 22568788, compound

HRID 51798Notes

Reaction equation

HRID 51798 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[C:5]([CH3:11])[CH:4]=1)#[CH:2].C(O)(=O)C1C=CC=CC=1.[CH2:21]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1)[CH3:22]>C(N(CC)CC)C.[Cu]I.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>[OH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:28]2[CH:29]=[CH:30][C:25]([C:24]([O:23][CH2:21][CH3:22])=[O:32])=[CH:26][CH:27]=2)=[CH:4][C:5]=1[CH3:11]

Participants

6

Reactant 2

HCID 22568989(4-Ethynyl-2-methyl-phenyl)-methanol2×HCID 69887287Ethyl-4-iodo-benzoate benzoate2×

Product 1

HCID 22568788HCID 22568788, compoundYield 100.4%

Reagents, catalysts & solvents 3

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

Procedure

Using General Procedure F; (4-ethynyl-2-methyl-phenyl)-methanol (Intermediate 136, 100.0 mg, 0.44 mmol) and ethyl-4-iodo benzoate (Reagent A, 125.0 mg, 0.45 mmol) in triethyl amine (4 mL) was treated with copper(I)iodide (29 mg, 0.15 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (102 mg, 0.15 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (20-40% EtOAc-hexanes) afforded 130.0 mg (99%) of the title compound as an orange solid.

Workup

  1. customsparged with argon for 5 minutes

Sources & evidence

ORD record
ord-deb05f02961c4e27b3b4bff1e815238b
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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