Sodium Hydroxide → (6-Hydroxy-2-(4-hydroxyphenyl)benzo(b)thien-3-yl)(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)methanone

HRID 2198608Notes

Reaction equation

HRID 2198608 reaction equation
Cl.CS([O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:30])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:18][CH:17]=3)=[C:13]([C:31]3[CH:36]=[CH:35][C:34]([O:37]S(C)(=O)=O)=[CH:33][CH:32]=3)[S:12][C:11]=2[CH:42]=1)(=O)=O.[OH-].[Na+]>C(O)C>[OH:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:30])[C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29]4)=[CH:20][CH:21]=3)=[C:13]([C:31]3[CH:32]=[CH:33][C:34]([OH:37])=[CH:35][CH:36]=3)[S:12][C:11]=2[CH:42]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1317128666-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Product 1

HCID 104946(6-Hydroxy-2-(4-hydroxyphenyl)benzo(b)thien-3-yl)(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 5 g. portion of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride, was dissolved in 125 ml. of denatured ethanol and 15 ml. of 5 N sodium hydroxide, and the mixture was stirred under reflux for one hour. The ethanol was then evaporated away under vacuum, and the residue was dissolved in water. The mixture was then made acid with 1 N hydrochloric acid, and was then made basic with sodium bicarbonate. The basic solution was extracted three times with 100 ml. portions of ethyl acetate, dried over magnesium sulfate, filtered and evaporated to an oil, 3.6 g., under vacuum. The oil was shown by thin layer chromatography to contain the desired product by comparison with authentic samples. It was purified further by chromatography on silica gel by elution with 6% methanol in chloroform. The size of the column was 3.5×2.5 cm., and 20 ml. fractions were collected. Fractions 31 through 150 contained 2.4 g. of partially purified product, which was identified by thin layer chromatographic comparison with an authentic sample of the desired product.

Workup

  1. temperatureunder reflux for one hour
  2. customThe ethanol was then evaporated away under vacuum
  3. dissolutionthe residue was dissolved in water
  4. extractionThe basic solution was extracted three times with 100 ml
  5. dry with materialportions of ethyl acetate, dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to an oil, 3.6 g
  8. customIt was purified further by chromatography on silica gel by elution with 6% methanol in chloroform
  9. customfractions were collected

Sources & evidence

ORD record
ord-964d675e3df74010ae6785f9454ae000
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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