Methanol → HCID 69555535, compound

HRID 1826425Notes

Reaction equation

HRID 1826425 reaction equation
O.[OH-].[Li+].[C:4]([C:6]1[CH:7]=[C:8](/[C:12](/[CH3:19])=[CH:13]/[C:14]([O:16]CC)=[O:15])[CH:9]=[CH:10][CH:11]=1)#[N:5].CO>O1CCCC1.O>[C:4]([C:6]1[CH:7]=[C:8](/[C:12](/[CH3:19])=[CH:13]/[C:14]([OH:16])=[O:15])[CH:9]=[CH:10][CH:11]=1)#[N:5]

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 23660557HCID 23660557, compound

Product 1

HCID 69555535HCID 69555535, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of lithium hydroxide monohydrate (10.8 g, 0.26 mol) in tetrahydrofuran (100 ml) and water (100 ml) was added crude ethyl (E)-3-(3-cyanophenyl)-2-butenoate (Preparation 31) in tetrahydrofuran (150 ml). The resultant mixture was made homogeneous by-the addition of methanol (approx. 50 ml), and then stirred at room temperature for 16 h. The mixture was concentrated in vacuo and acidified with 2N hydrochloric acid, following which a solid precipitated. The solid was collected by suction filtration, washing with cold water. The solid was then dried and recrystallised from acetonitrile.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customprecipitated
  3. filtrationThe solid was collected by suction filtration
  4. washwashing with cold water
  5. customThe solid was then dried
  6. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-dc9ec74cfd8648f19fbf1fa981c20eec
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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