Diisobutylaluminumhydride → (2E)-3-(4-tert-Butyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-en-1-ol
Reaction equation
[F:1]/[C:2](=[C:8](/[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[O:16][C:15]([CH3:23])([CH3:22])[CH:14]=[C:13]2[C:24]([CH3:27])([CH3:26])[CH3:25])\[CH3:9])/[C:3](OCC)=[O:4].[H-].C([Al+]CC(C)C)C(C)C>>[C:24]([C:13]1[C:12]2[C:17](=[CH:18][C:19]([O:20][CH3:21])=[C:10](/[C:8](/[CH3:9])=[C:2](/[F:1])\[CH2:3][OH:4])[CH:11]=2)[O:16][C:15]([CH3:23])([CH3:22])[CH:14]=1)([CH3:27])([CH3:25])[CH3:26]Participants
3
Procedure
Following General Procedure L, ethyl (2E)-fluoro-3-(4-tert-butyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)but-2-enoate (Compound 70, 148 mg, 0.39 mmol) and diisobutylaluminum hydride (1 M in dichloromethane, 1.1 mL, 1.1 mmol) were reacted to give the title compound as yellow solid after purification by flash chromatography (silica gel, 1:9 to 1:4 ethyl acetate/hexane).