Lithium Hydroxide → 194608-80-5

HRID 342765Notes

Reaction equation

HRID 342765 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([O:34]C)=[O:33])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]2[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][O:19][C:15]=2[C:14]=1[CH2:28][CH2:29][CH3:30].[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:31][C:32]([OH:34])=[O:33])[CH:5]=[CH:6][C:7]=1[S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]2[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][O:19][C:15]=2[C:14]=1[CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15840674HCID 15840674, compound

Product 1

HCID 9891946194608-80-5

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-chloro-4-(3-(3-phenyl-7-propylbenzofuran-6-yloxy)propylthio)-phenylacetate (3.72 g, 7.31 mmol) prepared in last step and aqueous lithium hydroxide(1.0M; 14.62 ml; 14.62 mmol) in methanol (25 ml) was refluxed for 1 hr. The mixture was partitioned between isopropyl acetate and pH4 buffer. The organic was dried over sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by chromatography (silica gel, 50% methylene chloride in hexane) to afford the title compound. M.P: 143° C. ESI-MS: m/e-495(M+1)

Workup

  1. temperaturewas refluxed for 1 hr
  2. customThe mixture was partitioned between isopropyl acetate and pH4 buffer
  3. dry with materialThe organic was dried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by chromatography (silica gel, 50% methylene chloride in hexane)

Sources & evidence

ORD record
ord-702b7fddd92c4e96aef65430aa960667
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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