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

HRID 1393093Notes

Reaction equation

HRID 1393093 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 EtOAc. 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/EtOAc=8/2), yielded 9.54 g of the title compound as light brown oil, MS: 248.2 (M)+.

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-18ea5ef5d55549cbae844e0804956673
Source dataset
uspto-grants-2008_03
Patent number
US07345067B2

Reaction notes

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