Hydrochloric Acid → HCID 15840673, compound

HRID 342761Notes

Reaction equation

HRID 342761 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([O:32]C)=[O:31])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:22]([CH2:23][CH2:24][CH3:25])=[C:21]2[C:16]([CH:17]=[C:18]([CH2:27][CH3:28])[C:19](=[O:26])[O:20]2)=[CH:15][CH:14]=1.[OH-].[K+].CO.Cl>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:29][C:30]([OH:32])=[O:31])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[C:22]([CH2:23][CH2:24][CH3:25])=[C:21]2[C:16]([CH:17]=[C:18]([CH2:27][CH3:28])[C:19](=[O:26])[O:20]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 15840672HCID 15840672, compound

Product 1

HCID 15840673HCID 15840673, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
30 °C

Procedure

To a solution of methyl 3-chloro-4-(3-ethyl-8-propyl-7-coumarinoxy)propylthio)phenylacetate (Example 3; 30 mg, 0.0613 mmol) 1.0 mL methanol:water (2:1) was added a 0.5M solution of potassium hydroxide in methanol (0.61 mL, 0.3061 mmol). The mixture was heated to 30° C. for two hours at which time the mixture was acidified to pH=3 with 1M hydrochloric acid. The aqueous solution was extracted with ethyl acetate and the combined organics were dried over magnesium sulfate, filtered, and the crude residue was purified by flash chromatography on silica gel (30% ethyl acetate/hexane/1% acetic acid) which provided the title compound

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. dry with materialthe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe crude residue was purified by flash chromatography on silica gel (30% ethyl acetate/hexane/1% acetic acid) which

Sources & evidence

ORD record
ord-600c286a0c6f4008a4727f2d255022f1
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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