[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:14]=[C:13]([C:15](C)(C)[O:16][SiH2]C(C)(C)C)[CH:12]=[C:11]([C:24](C)(C)[O:25][SiH2]C(C)(C)C)[CH:10]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[C:11]([CH2:24][OH:25])[CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1To a cooled (0° C.) solution of 6-[3,5-Bis-(tert-butyl-dimethyl-silyloxymethyl)-phenyl]-hex-5-ynoic acid methyl ester (140 mg) in anhydrous tetrahydrofurane (0.3 mL) was slightly added a solution of tetrabutylammonium fluoride 1 M in THF (716 μL). After 75 min at rt, ethyl acetate (20 mL) was added and the organic phase was washed three times with water (5 mL) and once with a saturated aqueous solution of sodium chloride (5 mL), dried over sodium sulfate and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 15 g column, Si60 15-40 μm), using gradient elution with a mixture of heptane (A)/ethyl acetate (B), (gradient: 50% A: 50% B down to 10% A: 90% B) to give 6-(3,5-Bis-hydroxymethyl-phenyl)-hex-5-ynoic acid methyl ester (64.3 mg) as a pale yellow oil. LC/MS (Method A3): ES: m/z 263 (M+H)+; RT=0.62 min
Loading…
