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

HRID 613129Notes

Reaction equation

HRID 613129 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-9e7c71499c544a47ae0dd0a5cf25cfe2
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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