Water → HCID 20253976, compound

HRID 638256Notes

Reaction equation

HRID 638256 reaction equation
[OH-].[K+].O.[C:4]([C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][OH:25])=[CH:17][CH:16]=1)([O:6]C)=[O:5]>C(O)C>[C:4]([C:8]1[S:9][CH:10]=[CH:11][C:12]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:26])[CH2:22][CH2:23][CH2:24][OH:25])=[CH:17][CH:16]=1)([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 20253978HCID 20253978, compound

Product 1

HCID 20253976HCID 20253976, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 14.59 g of potassium hydroxide, 15 ml of water, and 60 ml of 95% ethanol was added a solution of 8.68 g of 4-[4-(2-carbomethoxy-3-thienylmethoxy)phenyl]pentanol and 30 ml of 95% ethanol. The stirred solution was heated under reflux for five hours, allowed to stand overnight at ambient temperature, and concentrated. The residue was diluted with 500 ml of water, and the solution was acidified with concentrated hydrochloric acid. An oil separated. The mixture was extracted with ether (2×250 ml) and the combined organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. A solution of the residue and toluene was filtered through anhydrous sodium sulfate and the filtrate was concentrated to afford 6.89 g (82.7%) of product as an oil, dried at 60° C. in vacuo.

Workup

  1. temperatureThe stirred solution was heated
  2. temperatureunder reflux for five hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with 500 ml of water
  5. customAn oil separated
  6. extractionThe mixture was extracted with ether (2×250 ml)
  7. dry with materialthe combined organic phase was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. filtrationA solution of the residue and toluene was filtered through anhydrous sodium sulfate
  11. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5d85088c59e34c86a80202b03c5c5972
Source dataset
uspto-grants-1985_12
Patent number
US04560701

Reaction notes

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