Methanol → HCID 69555535, compound

HRID 428918Notes

Reaction equation

HRID 428918 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. From the first crop, 15.8 g (49% over 2 steps) of the pure E-isomer was isolated.

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
  7. customFrom the first crop, 15.8 g (49% over 2 steps) of the pure E-isomer was isolated

Sources & evidence

ORD record
ord-8fe54fcd55354fb083fb657731f3200f
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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