Sulfuric Acid → HCID 54569995, compound

HRID 257330Notes

Reaction equation

HRID 257330 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

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 19783080HCID 19783080, compound

Product 1

HCID 54569995HCID 54569995, compoundYield 73.5%

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).

Workup

  1. customsynthesized in Example 1
  2. extractionextracted with ethyl acetate
  3. washthe extract was successively washed with saturated saline
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-be02a21cd978486d86de4bdc35b9eabb
Source dataset
uspto-grants-1993_11
Patent number
US05262385

Reaction notes

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