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

HRID 1700885
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HRID 1700885 반응식
[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]
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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 1,4-dioxane (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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e64aeeae9b4c41fdb65229373f0741ce
출처 데이터셋
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06350892B1

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