Triphenylphosphine → 1,1-(Ethylenedioxy)-4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(3-nitrophenylethynyl)cyclohexane

HRID 343549

Reaktionsgleichung

Reaktionsgleichung von HRID 343549
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[CH:26])[CH2:20][CH2:19][C:18]4([O:24][CH2:23][CH2:22][O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:28]1[C:29]([N+:35]([O-:37])=[O:36])=[C:30](O)[CH:31]=[CH:32][CH:33]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1CCCCC1.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH2:23]1[CH2:22][O:21][C:18]2([CH2:19][CH2:20][C:15]([C:9]3[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:8]=3)([C:25]#[C:26][C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([N+:35]([O-:37])=[O:36])[CH:28]=3)[CH2:16][CH2:17]2)[O:24]1

Komponenten

8

Edukt 3

HCID 11776TriphenylphosphineHCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexaneHCID 537808793-Iodo-2-nitrophenol

Produkt 1

HCID 544563801,1-(Ethylenedioxy)-4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(3-nitrophenylethynyl)cyclohexane

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8082PiperidineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane (0.14 g, 0.38 mmol) and 3-iodonitrophenol (0.10 g, 0.38 mmol) in piperidine (2 mL) under an argon atmosphere were added tetrakis(triphenylphosphine)palladium(0) (0.02 g, 4%), copper(I) iodide (0.005 g, 6%) and a small crystal of triphenylphosphine. After heating at 70° C. for 0.33 h, the mixture was diluted with dichloromethane, was washed with 1N hydrochloric acid, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 2:8 ethyl acetate:hexanes, provided 1,1-(ethylenedioxy)-4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(3-nitrophenylethynyl)cyclohexane as an orange wax. 1H-NMR (400MHz, CDCl3) δ 8.29 (s, 1H), 8.16 (d, J=9.0 Hz, 1H), 7.75 (d, J=7.9 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 7.26 (d, J=2 Hz, 1H), 7.14 (dd, J=8.3, 2 Hz, 1H), 6.86 (d, J=8.3 Hz, 1H), 4.82 (m, 1H), 4.01 (s, 4H), 3.85 (s, 3H), 2.18 (m, 4H), 2.07 (m, 2H), 1.93 (m, 4H), 1.85 (m, 4H), 1.6 (m, 2H).

Aufarbeitung

  1. washwas washed with 1N hydrochloric acid
  2. dry with materialwas dried (magnesium sulfate)
  3. customwas evaporated
  4. customPurification by flash chromatography
  5. washeluting with 2:8 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ae27abb7487247db82477e79e17f1909
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861421

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