Lithium Hydroxide → HCID 21017824, compound

HRID 1743940

Reaction equation

HRID 1743940 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C@H:9]2[C:15]([O:17]C)=[O:16])=[CH:4][CH:3]=1.[OH-].[Li+].Cl.[Cl-].[Na+].O>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C@H:9]2[C:15]([OH:17])=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 68520286Methyl trans-2-(4-chlorophenyl)-5-oxocyclohexanecarboxylateHCID 131718760Hydrochloric acid brine

Product 1

HCID 21017824HCID 21017824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 0.435 g (1.63 mmol) of methyl trans-2-(4-chlorophenyl)-5-oxocyclohexanecarboxylate (described in Step B of Example 1) and 1 N lithium hydroxide (3.26 mL, 3.26 mmol) in tetrahydrofuran (3.3 mL) was heated at reflux for approximately 1 h. After cooling to room temperature, the reaction mixture was poured into 1 N hydrochloric acid/brine (1:1) and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residual crude title compound was used without further purification in the subsequent reaction.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 1 h
  3. extractionextracted three times with methylene chloride
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residual crude title compound was used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-8b3ecda7dbf445b9a8b5902406e978b7
Source dataset
uspto-grants-2006_03
Patent number
US07012084B2

Linked notes

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