Triethylamine → 2-(3-Methoxy-prop-1-ynyl)-phenoxy-acetic acid ethyl ester

HRID 1242277Notes

Reaction equation

HRID 1242277 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1I)[CH3:2].[CH3:15][O:16][CH2:17][C:18]#[CH:19].CCN(CC)CC>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.C(#N)C>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:19]#[C:18][CH2:17][O:16][CH3:15])[CH3:2]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 693933-MethoxypropyneHCID 11808921Acetic acid, (2-iodophenoxy)-, ethyl ester

Product 1

HCID 670722722-(3-Methoxy-prop-1-ynyl)-phenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 3

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

Procedure

A three neck reaction flask was successively charged with 12.65 g (41.3 mmol) of the above prepared (2-iodo-phenoxy)-acetic acid ethyl ester, 128 ml of acetonitrile, 5.793 g (2 eq.) of 3-methoxy-1-propyne, 17.28 ml (3 eq.) of NEt3, 1.45 g (0.05 eq.) of (PPh3)2PdCl2, and 0.394 g (0.05 eq.) of CuI. After stirring for 4 h the bulk of the solvent was removed i. V. and the residue distributed between HCl and AcOEt. Washing of the organic layer with cold water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=8/2), yielded 9.54 g of the title compound as light brown oil.

Workup

  1. additionA three neck reaction flask was successively charged with 12.65 g (41.3 mmol) of the
  2. customwas removed i
  3. washWashing of the organic layer with cold water and brine
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7078bc1fa8c344589753faa635a55d3e
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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