Sodium Hydroxide → (2E)-4-(tert-butoxy)-4-oxobut-2-enoic acid

HRID 1766135Notes

Reaction equation

HRID 1766135 reaction equation
[C:1]([O:5][C:6](=[O:14])/[CH:7]=[CH:8]/[C:9]([O:11]CC)=[O:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Li+].[Cl-].OS([O-])(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6](=[O:14])/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 516920Potassium bisulfateHCID 11469708HCID 11469708, compound

Product 1

HCID 5797551(2E)-4-(tert-butoxy)-4-oxobut-2-enoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-1 (340 mg, 1.7 mmol) was stirred for 1 h at rt with a solution comprised of 4 mL THF, and 4 mL of a solution containing 1 M NaOH and 1 M LiCl. The resulting mixture was acidified to pH 3-4 with 1 M KHSO4 and extracted twice with 30 mL of EtOAc. The extract was washed with 30 mL of brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting material was subjected to silica gel flash chromatography using a gradient of 5–10% methanol in DCM to yield 240 mg (82% yield) of 4-2.

Workup

  1. extractionextracted twice with 30 mL of EtOAc
  2. washThe extract was washed with 30 mL of brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85aa148c332a4591b2283321e9ae9c37
Source dataset
uspto-grants-2007_06
Patent number
US07230005B2

Reaction notes

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