Hydrochloric Acid → 2-[4-[4-Hydroxy-5-(2-isopropylphenyl)sulfanyl-6-oxo-pyran-2-yl]phenoxy]acetic acid

HRID 2394051Notes

Reaction equation

HRID 2394051 reaction equation
O1CCCC1.C([O:8][C:9](=[O:36])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][C:20](=[O:35])[C:21]([S:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH:32]([CH3:34])[CH3:33])=[C:22]([OH:24])[CH:23]=2)=[CH:14][CH:13]=1)C.[OH-].[Na+].Cl>O>[OH:24][C:22]1[CH:23]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:9]([OH:36])=[O:8])=[CH:17][CH:16]=2)[O:19][C:20](=[O:35])[C:21]=1[S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:32]([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 54690953Ethyl 2-[4-[4-hydroxy-5-(2-isopropylphenyl)sulfanyl-6-oxo-pyran-2-yl]phenoxy]acetate

Product 1

HCID 546813172-[4-[4-Hydroxy-5-(2-isopropylphenyl)sulfanyl-6-oxo-pyran-2-yl]phenoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a tetrahydrofuran (10 ml) solution of 4-[4-Hydroxy-5-[(2-isopropylphenyl)thio]-6-oxo-6H-pyran-2-yl]phenoxy acetic acid ethyl ester (0.319 g. 0.75 mmol) was added 1N sodium hydroxide (1.80 mL, 1.81 mmol). The reaction was stirred for 1.5 h, and then water (10 ml) was added followed by acidification with conc. hydrochloric acid to pH 2. The aqueous layer was then extracted 2× with ethyl acetate (100 ml). the combined organic extracts were then washed with saturated sodium chloride and dried over anhydrous magnesium sulfate. After evaporation of the solvents in vacuo, the crude product was purified by column chromatography (silica gel--230 to 400 mesh) using 94/5/1 methylene chloride/methanol/acetic acid as the eluent. m.p. 217° C.; (dec.); 1H NMR (400 MHz, DMSO-d6) δ 1.25 (d, 6H), 3.42 (m, 1H), 4.79 (s, 2H), 6.75 (s, 1H), 6.90 (d, 1H), 7.06 (m, 4H), 7.26 (d, 1H), 7.79 (d, 2H).

Workup

  1. extractionThe aqueous layer was then extracted 2× with ethyl acetate (100 ml)
  2. washthe combined organic extracts were then washed with saturated sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvents in vacuo
  5. customthe crude product was purified by column chromatography (silica gel--230 to 400 mesh)

Sources & evidence

ORD record
ord-ec8383785d604078b13c3f01796631a6
Source dataset
uspto-grants-1998_09
Patent number
US05808062

Reaction notes

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