Triethylamine → (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acryloyl azide

HRID 1852060

Reaktionsgleichung

Reaktionsgleichung von HRID 1852060
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[C:7](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)=[CH:8][CH:9]=[CH:10][C:2]1=2.C1(P([N:30]=[N+:31]=[N-:32])(C2C=CC=CC=2)=O)C=CC=CC=1.CCN(CC)CC>C1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[C:7](/[CH:11]=[CH:12]/[C:13]([N:30]=[N+:31]=[N-:32])=[O:15])=[CH:8][CH:9]=[CH:10][C:2]1=2

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 5343159(E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acrylic acid

Produkt 1

HCID 86683170(E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acryloyl azideAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

(E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acrylic acid (5 g, 24.25 mmol), diphenylphosphoryl azide (4.96 mL, 23.04 mmol), and Et3N (6.76 mL, 48.5 mmol) were dissolved in benzene and stirred for 16 h. The solution was concentrated under vacuum and the residue was purified by silica gel chromatography using 20% EtOAc/Hexanes to give 4.5 g of (E)-3-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)acryloyl azide as a yellow solid, which was taken into PhCH2Ph (50 mL). The resulting solution was slowly heated to 80° C. for 1 h and then to reflux for 3 h. After cooling to rt, the solid was collected washing with benzene to give 3.5 g of the desired product 2,3-dihydro-[1,4]dioxino[2,3-f]isoquinolin-7-ol as a solid. 1H NMR (400 MHz, CD3OD) δ ppm 4.37 (m, 4H), 6.83 (d, J=7.09 Hz, 1H), 7.02 (d, J=8.80 Hz, 1H), 7.12 (d, J=7.34 Hz, 1H), 7.79 (d, J=8.80 Hz, 1H); MS: (M+H)+ 204.

Aufarbeitung

  1. concentrationThe solution was concentrated under vacuum
  2. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f4bfd13f1eab46d4a6d799a38b10c652
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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