Hydrochloric Acid → HCID 53963642, compound

HRID 377088Notes

Reaction equation

HRID 377088 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH2:20][F:21])[C@@H:7]2[C@H:8]([O:11]C(OCC)C)[O:9][CH:10]=1)=[O:4].Cl.O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH2:20][F:21])[C@@H:7]2[CH:8]([OH:11])[O:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 56974884HCID 56974884, compound

Product 1

HCID 53963642HCID 53963642, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

670 mg of the above (1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-(fluoromethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester were dissolved in tetrahydrofuran followed by addition of 2N aqueous hydrochloric acid and stirring for 2 hours at room temperature. The reaction mixture was neutralized after adding water, and then extracted with ethyl acetate. After washing the organic phase with brine, it was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a pale yellow oil from the hexane-ether eluate in the form of (4aS,7aR)-7-(fluoromethyl)-1-hydroxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester (500 mg, yield: 98%). The physicochemical properties of this compound are described below.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing the organic phase with brine, it
  3. dry with materialwas dried over magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fb525104f1a1467e81d9bdc013fb7b1b
Source dataset
uspto-grants-2000_02
Patent number
US06022888

Reaction notes

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