Octanal → 1-(4-(2-Methoxyethenyl)phenyl)-1-octanol
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][O:10][CH3:11])=[CH:4][CH:3]=1.[CH:12](=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>>[CH3:11][O:10][CH:9]=[CH:8][C:5]1[CH:6]=[CH:7][C:2]([CH:12]([OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:3][CH:4]=1Participants
3
Procedure
By the method of example 28, 1-bromo-4-(2-methoxyethenyl)benzene is prepared, lithiated, and reacted with octanal to provide 1-(4-(2-methoxyethenyl)phenyl)-1-octanol as a yellow oil after chromatography. The hydroxyl group is protected as the t-butyldimethylsilyl ether in the usual fashion, and the enol ether is then cleaved with chlorotrimethylsilane and sodium iodide as described in example 33. The resulting aryl acetaldehyde is obtained as an oil, and is immediately condensed with glyoxylic acid, by the method described in example 1(C). Under the reaction conditions, the silyl ether is simultaneously eliminated, and chromatography provides the title compound as a tan solid, mp 98°-99° after trituration with hot hexane.
Sources & evidence
- ORD record
- ord-0ed8e3f4b4674c9a9cbb90f008026447