Bromocyclopentane → 2-[4-(Cyclopentylthio)-2-fluoro-phenyl]propionic acid

反応式

[F:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([O:12]C)=[O:11].Br[CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:16]1([S:8][C:6]2[CH:5]=[CH:4][C:3]([CH:9]([CH3:14])[C:10]([OH:12])=[O:11])=[C:2]([F:1])[CH:7]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

実験手順

A solution of compound (9) (0.53 g, 2.5 mmol), bromocyclopentane (0.32 mL, 3.0 mmol), and potassium carbonate (1.2 g, 8.8 mmol) in dry DMF (5 mL) was treated in the same manner as in Example 7. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution followed by conventional hydrolysis to give 0.64 g (90%) of compound (17) of interest as white solid.