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Triphenylphosphine → HCID 54086791, Verbindung

HRID 343574
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 343574
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[CH:23])[CH2:20][CH2:19][C:18](=[O:21])[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:25]1[CH:26]=[C:27]([C:31]2[O:35][C:34]([CH3:36])=[N:33][N:32]=2)[CH:28]=[CH:29][CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.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>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:29]4[CH:30]=[CH:25][CH:26]=[C:27]([C:31]5[O:35][C:34]([CH3:36])=[N:33][N:32]=5)[CH:28]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 108289304-(3-Cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-oneHCID 19349977HCID 19349977, Verbindung

Produkt 1

HCID 54086791HCID 54086791, VerbindungAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynylcyclohexan-1-one (0.100 g, 0.32 mmol) and 5-(3-iodophenyl)-2-methyl-[1,3,4]oxadiazole (0.0915 g, 0.32 mmol) in dry triethylamine (3.5 mL) was treated under argon with a mixture of tetrakis(triphenylphosphine)palladium (0.016 g, 0.013 mmol), cuprous iodide (0.0033 g, 0.017 mmol), and triphenylphosphine (a small crystal) at 75° C. for 1 h. The reaction mixture was concentrated in vacuo, the residue was extracted into methylene chloride and the organic phase was washed with cold dilute hydrochloric acid, water, brine and was dried (sodium sulfate). Purification by chromatography (silica, 10 to 20% ethyl acetate in methylene chloride) followed by drying at 50° C. in vacuo afforded the titled compound as a white powder (0.068 g, 45%), mp 139°-141° C. Anal. (C29H30N2O4.1/3H2O) calcd: C 73.09, H 6.49, N 5.88, found: C 73.07, H 6.35, N 5.79. 1H-NMR (400 MHz, CDCl3) δ 8.15 (t, J=1.6 Hz, 1H), 8.01 (d-t, J=1.4 Hz, J=7.9 Hz, 1H), 7.62 (d-d, J=1.5 Hz, J=7.8 Hz, 1H), 7.49 (t, J=7.9 Hz), 7.21 (d, J=2.3, 1H), 7.14 (d-d, J=8.5 Hz, J=2.4 Hz, 1H), 6.88 (d, J=8.5, 1H), 4.82 (p, J=4.2 Hz, 1H), 3.86 (s, 3H), 3.04 (d-t, J=6.1 Hz, J=14.2, 2H), 2.64 (s, 3H), 2.51 (d,br, J=15.0, 2H), 2.42-2.32 (m, 2H), 2.27 (d-t, J=2.8 Hz, J=14.2 Hz, 2H), 2.00-1.5 (m, 9H with H2O).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionthe residue was extracted into methylene chloride
  3. washthe organic phase was washed with cold dilute hydrochloric acid, water, brine
  4. dry with materialwas dried (sodium sulfate)
  5. customPurification by chromatography (silica, 10 to 20% ethyl acetate in methylene chloride)
  6. customby drying at 50° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b37a9c5627514a519cc81b3ee9bc07dc
Quelldatensatz
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05861421

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