Sodium Hydroxide → HCID 66993571, compound

HRID 251645Notes

Reaction equation

HRID 251645 reaction equation
C[O:2][C:3](=[O:25])[CH:4]=[CH:5][C:6]1[C:7]([CH3:24])=[N:8][C:9]([C:14]2[C:19]([CH2:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:22][CH3:23])=[CH:10][C:11]=1[CH2:12][CH3:13].[OH-].[Na+]>CCO>[CH2:22]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([CH2:20][CH3:21])[C:14]=1[C:9]1[N:8]=[C:7]([CH3:24])[C:6]([CH:5]=[CH:4][C:3]([OH:25])=[O:2])=[C:11]([CH2:12][CH3:13])[CH:10]=1)[CH3:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66994286HCID 66994286, compound

Product 1

HCID 66993571HCID 66993571, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the ester above (403 mg, 1.2 mmol) in EtOH (5 mL) is treated with NaOH (5 mL of 1 N solution in water). The mixture is heated for 2 hours at 100° C. and concentrated in vacuo. The residue is diluted with EtOAc and acidified to pH 4 with 1 N-HCl. The layers are separated and the aqueous layer is extracted with EtOAc. The combined organic layers are washed with saturated brine, dried (Na2SO4), and concentrated to yield 3-[6-(2,6-diethyl-phenyl)-4-ethyl-2-methylpyridin-3-yl]-acrylic acid as a white foam. 1H NMR (CDCl3) 7.64 (d, 1H), 7.29 (dd, 1H), 7.15 (d, 2H), 7.09 (s, 1H), 6.20 (d, 1H), 2.76 (q, 2H), 2.71 (s, 3H), 2.33 (m, 4H), 1.22 (t, 3H), 1.04 (m, 6H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue is diluted with EtOAc
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc
  5. washThe combined organic layers are washed with saturated brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a6360cd8406d4898a4d3a6deb5e86706
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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