Hydrochloric Acid → HCID 15840671, compound

HRID 342757Notes

Reaction equation

HRID 342757 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]([C:17]([CH2:27][CH3:28])=[CH:18][C:19](=[O:26])[O:20]2)=[CH:15][CH:14]=1.[OH-].[K+].Cl>CO.O.CO>[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]([C:17]([CH2:27][CH3:28])=[CH:18][C:19](=[O:26])[O:20]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15840670HCID 15840670, compound

Product 1

HCID 15840671HCID 15840671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 3-chloro-4-(3-(4-ethyl-8-propyl-7-coumarinoxy)propylthio)phenylacetate (Example 1; 82 mg, 0.1677 mmol) in 1.2 mL methanol:water (1:1) was added a 0.5M solution of potassium hydroxide in methanol. The mixture was heated to 40° C. for two hours at which time the mixture was acidified to pH=3 with 1M aqueous 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-a30c04ac4b43426089b48b5e595810af
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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