2,6-Di-tert-butyl-4-methylphenol → 3-[4-[2-(N-Dodecyl-N-methylamino)ethoxy]-2-vinylphenyl]propanoic acid, methyl ester

HRID 1383904Notes

Reaction equation

HRID 1383904 reaction equation
[CH2:1]([N:13]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[C:20](OS(C(F)(F)F)(=O)=O)[CH:19]=1)[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:38](C([Sn])=C(CCCC)CCCC)[CH2:39]CC.[Cl-].[Li+].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>O1CCOCC1.C(OCC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:13]([CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[C:20]([CH:38]=[CH2:39])[CH:19]=1)[CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 4

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 53438229Tri(butyl)vinyltinHCID 867571193-[4-[2-(N-Dodecyl-N-methylamino)ethoxy]-2-[trifluoromethanesulfonyloxy]phenyl]propanoic Acid, Methyl Ester

Product 1

HCID 867571183-[4-[2-(N-Dodecyl-N-methylamino)ethoxy]-2-vinylphenyl]propanoic acid, methyl esterYield 82%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-[4-[2-(N-dodecyl-N-methylamino)ethoxy]-2-[trifluoromethanesulfonyloxy]-phenyl]propanoic acid, methyl ester (250 mg, 0.48 mmol) in 1,4dioxane (2.5 ml) were added tributylvinyltin (1.2 ml, 4.0 mmol), lithium chloride (123 mg, 1.44 mmol), tetrakis(triphenylphosphine)-palladium(0) (10 mg) and 2,6-di-tert-butyl-4-methylphenol (10 mg). The resulting mixture was then stirred at 100° C. for 5 h. After cooling to r.t., the mixture was diluted with diethyl ether, washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (diethyl ether/acetone 100:0 to 80:20) to afford the title compound (170 mg, 80%) as a yellow oil.

Workup

  1. temperatureAfter cooling to r.t.
  2. washwashed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (diethyl ether/acetone 100:0 to 80:20)

Sources & evidence

ORD record
ord-0fd06fd682b64d01bbb41414cd9da783
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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