Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 2-[3-(3-bromophenyl)cyclobutylidene]acetate

HRID 30598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 30598
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][C:10](=O)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:13]([O:15][C:16](=[O:37])[CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:14]>ClCCl>[CH2:13]([O:15][C:16](=[O:37])[CH:17]=[C:10]1[CH2:11][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:9]1)[CH3:14]

Komponenten

4

Edukt 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 177501013-(3-Bromophenyl)cyclobutan-1-one

Produkt 1

HCID 59790338Ethyl 2-[3-(3-bromophenyl)cyclobutylidene]acetateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-(3-bromophenyl)cyclobutanone (2.03 g 9.02 mmol) and triphenylphosphoranylidene acetic acid ethyl ester (15.72 gms 45.12 mmol) dichloromethane was irradiated in a CEM Discover™ microwave instrument for 30 minutes at 120° C. Pressure reached a maximum of 180 PSI. Standard work-up procedures followed by purification by column chromatography (isocratic; 10% diethyl ether in hexanes) afforded [3-(3-bromophenyl)cyclobutylidene]acetic acid ethyl ester as an oil, 2.37 g (89% yield), 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (t, J=7.1 Hz, 3 H) 2.89-3.00 (m, 1 H) 3.03-3.11 (m, 1 H) 3.16-3.27 (m, 1 H) 3.46-3.57 (m, 1 H) 3.63 (q, J=8.0 Hz, 1 H) 4.08 (q, J=7.0 Hz, 2 H) 5.71 (q, J=2.9 Hz, 1 H) 7.25-7.35 (m, 2 H) 7.39-7.43 (m, 1 H) 7.48-7.52 (m, 1 H); MS (APPI) m/z 295 [M+H]+.

Aufarbeitung

  1. customStandard work-up procedures followed by purification by column chromatography (isocratic; 10% diethyl ether in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-252b40f7390847b594300747d626e7b6
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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