Sulfuric Acid → HCID 54569995, compound
Reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH3:13][O:14][C:15]([C:17]1([F:23])CC[CH2:19][CH:18]1O)=[O:16]>>[CH3:13][O:14][C:15]([C:17]1([F:23])[CH2:18][CH2:19][CH2:6][CH:5]1[O:4][C:1](=[O:3])[CH3:2])=[O:16]Participants
4
Procedure
0.32 g (3 mmol) of acetic anhydride and a catalytic amount of concentrated sulfuric acid were added at room temperature to 0.5 g (3 mmol) of 1-fluoro-2-hydroxycyclopentanecarboxylic acid methyl ester in cis form (compound number 2a) synthesized in Example 1, and the mixture was stirred for 5 hours. The reaction solution was poured into ice water and extracted with ethyl acetate, and the extract was successively washed with saturated saline, a saturated aqueous sodium bicarbonate solution and saturated saline. The ethyl acetate layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to obtain 0.45 g (yield: 72%) of the objective 2-acetoxy-1-fluoro-1-cyclopentanecarboxylic acid methyl ester in cis form (compound number 3a).