Potassium Hydroxide → HCID 22718039, compound

HRID 460457Notes

Reaction equation

HRID 460457 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:44]=[CH:43][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH2:33][CH2:34][CH2:35][C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38])([C:28]([O:30]CC)=[O:29])[C:23]([O:25]CC)=[O:24])=[CH:14][CH:13]=3)=[O:11])=[C:8]([C:45]3[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=3)[S:7][C:6]=2[CH:52]=1.[OH-].[K+]>C(O)C.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([C:12]3[CH:44]=[CH:43][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([CH2:33][CH2:34][CH2:35][C:36]([F:42])([F:41])[C:37]([F:38])([F:39])[F:40])([C:28]([OH:30])=[O:29])[C:23]([OH:25])=[O:24])=[CH:14][CH:13]=3)=[O:11])=[C:8]([C:45]3[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=3)[S:7][C:6]=2[CH:52]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 22718074HCID 22718074, compound

Product 1

HCID 22718039HCID 22718039, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Diethyl 2-[5-[4-[(6-hydroxy-2-(4-hydroxyphenyl)benzo-[b]thiophen-3-yl)carbonyl]phenoxy]pentyl]-2-(4,4,5,5,5-pentafluoropentyl)malonate (1.197 g, 1.59 mmol) was dissolved in ethanol (20 ml), and potassium hydroxide (3.58 g, 63.8 mmol) dissolved in water (10 ml) was then added. After stirring for 24 hours at 80° C., the reaction mixture was cooled to room temperature, concentrated under reduced pressure to remove ethanol, adjusted to pH 3 with 3N aqueous hydrochloric acid, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 2-[5-[4-[(6-hydroxy-2-(4-hydroxyphenyl)benzo-[b]thiophen-3-yl)carbonyl]phenoxy]pentyl]-2-(4,4,5,5,5-pentafluoropentyl)malonic acid (1.1 g) as a brown product, which was then used for the subsequent reaction without further purification.

Workup

  1. additionwas then added
  2. temperaturethe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customto remove ethanol
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9cba1fdac08a40c59dd33bd6b919e8b5
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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