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1-Tridecyne → HCID 53669740, Verbindung

HRID 986545
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 986545
Br[C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[CH:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:14]([C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1)#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 1177541-TridecyneHCID 8167732-Propenoic acid, 3-(4-bromophenyl)-, methyl ester

Produkt 1

HCID 53669740HCID 53669740, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysator
HCID 8471
Triethylamine
Lösungsmittel

Versuchsvorschrift

To a deaerated solution of methyl 4-bromocinnamate (9.64 g, 40 mmole) in dry triethylamine (120 ml) was added triphenylphosphine (308 mg) followed by 1-tridecyne (8.00 g, 45 mmole) and palladium (II) acetate (92 mg) under nitrogen. The mixture was heated to reflux for 24 hours, the reaction being followed by hplc. After this time the mixture was cooled and the precipitated triethylamine hydrobromide was filtered off and washed with a little triethylamine. The filtrate was evaporated to a red solid which was chromatographed on 220 g of silica eluting with petroleum ether [bp 60-80]-dichloromethane (3:2) to give 6.26 g (47%) of title compound as a pale yellow solid of mp (MeOH) 57°-59° C., υmax (mull) 1710, 1630, 1600, 1315, 1170, 1000, 830 cm-1, δ(CDCl3). 0.85 (3H, distorted t, terminal CH3), 1.28 (18H, m, alkylene chain), 2.38 (2 H, t, J 6.5 Hz, C≡C--CH2), 3.78 (3H, s, ester CH3), 6.37 (1H, d, J 16 Hz, =CHCO2), 7.42 (4H, near s, arom), 7.63 (1H, d, J 16 Hz, ArCH=)

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperatureAfter this time the mixture was cooled
  4. filtrationthe precipitated triethylamine hydrobromide was filtered off
  5. washwashed with a little triethylamine
  6. customThe filtrate was evaporated to a red solid which
  7. customwas chromatographed on 220 g of silica eluting with petroleum ether [bp 60-80]-dichloromethane (3:2)

Quellen und Nachweise

ORD-Eintrag
ord-56e8b5ed1ac340ea9a19c868ed210814
Quelldatensatz
uspto-grants-1987_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04713486

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