Methanol → HCID 59350816, compound

HRID 1644753Notes

Reaction equation

HRID 1644753 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([CH:15]([OH:26])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:27])[CH:11]=2)[CH:6]=1.[CH3:29]O>S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([CH:15]([C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[O:26][CH3:29])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:27])[CH:11]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 59350854HCID 59350854, compound

Product 1

HCID 59350816HCID 59350816, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of {6-fluoro-4-[hydroxy-(4-methanesulfonyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester (90 mg, 0.23 mmol) in methanol (5 mL) was added 3 drops of concentrated sulfuric acid. The mixture was heated at reflux overnight. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The collected organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 0-40% ethyl acetate in hexane) gave {6-fluoro-4-[(4-methanesulfonyl-phenyl)-methoxy-methyl]-naphthalen-2-yl}-acetic acid methyl ester (37.6 mg, 39%) as a clear oil. MS (ESI+) cald. for C22H21FO5S [(M+H)+] 416, obsd. 417.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customthe reaction mixture was partitioned between ethyl acetate and water
  4. dry with materialThe collected organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36a83a1c902f47faac822df932b69264
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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