Reaktion #1069215

ord-9fc8fd91084e422fa11a57f3d61f1d82

Reaktionsgleichung

CCOC(=O)c1[nH]c2ccccc2c1C=O
resultant compound
CCOC(=O)c1[nH]c2ccccc2c1C=O
Ethyl 3-Formylindole-2-carboxylate
[Br-].c1ccc([P+](CC2CCCCC2)(c2ccccc2)c2ccccc2)cc1
resultant compound
[Br-].c1ccc([P+](CC2CCCCC2)(c2ccccc2)c2ccccc2)cc1
(Cyclohexyl)methyltriphenylphosphonium Bromide
[Br-].c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
benzyltriphenylphosphonium bromide
CCOC(=O)c1[nH]c2ccccc2c1C=Cc1ccccc1
desired compound
Ausbeute 73.0%
CCOC(=O)c1[nH]c2ccccc2c1C=Cc1ccccc1
Ethyl 3-(2-Phenylethenyl)indole-2-carboxylate
Ausbeute 73.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using the procedure of Example 121 but replacing the resultant compound of Example 98 with the resultant compound of Example 97 and replacing the resultant compound of Example 120 with benzyltriphenylphosphonium bromide gave the desired compound in 73% yield after silica gel chromatography using 4:1 hexane/ethyl acetate. 1H NMR (CDCl3) δ 1.49 (t,J=7 Hz,3H), 4.48 (q,J=7 Hz,2H), 7.2-7.3 (m,2H), 7.35-7.45 (m,5H), 7.60 (br d,J=8 Hz,1H), 8.07 (d,J=16 Hz,1H), 8.16 (d,J=8 Hz,1H), 8.88 (br,1H). Mass spectrum: (M+H)+ =292.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04994477uspto-grants-1991_02