Sodium Hydroxide → HCID 69060272, compound

HRID 1436874Notes

Reaction equation

HRID 1436874 reaction equation
[C:1]([C:3]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH2:9][CH:10]=[CH2:11])[CH2:4][C:5]([O:7]C)=[O:6])#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH2:9][CH:10]=[CH2:11])[CH2:4][C:5]([OH:7])=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69066641HCID 69066641, compound

Product 1

HCID 69060272HCID 69060272, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-cyano-3-phenylhex-5-enoate (6.03 g, 26.3 mmol) in methanol (90 mL) was added 1M aqueous NaOH (29 mL, 29 mmol). After stirring overnight at room temperature, the reaction mixture was concentrated under vacuum. The residue was partitioned between EtOAc and water and the pH of the aqueous phase was adjust to pH 4 using 3N aqueous HCl. The organic extract was dried with Na2SO4, filtered, and concentrated under vacuum to provide the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 12.45 (br, 1H), 7.50 (d, J=1.6 Hz, 2H), 7.45 (t, J=1.9 Hz, 2H) 7.42 (t, J=1.7 Hz, 1H), 5.51 (m, 1H), 5.11 (m, 2H), 3.17 (s, 2H), 2.77 (m, 2H), 2.51 (s, 2H) ppm. ES MS M+1=216.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customThe residue was partitioned between EtOAc and water
  3. extractionThe organic extract
  4. dry with materialwas dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-62cbc4c9686f443fa234ba27a489b966
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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