Glutaric anhydride → 5-(Tert-butoxy)-5-oxopentanoic acid

HRID 1766130Notes

Reaction equation

HRID 1766130 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[C:7]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8]1>C1COCC1>[C:2]([O:4][C:7](=[O:14])[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])([CH3:5])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 23665647Potassium tert-butoxide

Product 1

HCID 114240215-(Tert-butoxy)-5-oxopentanoic acidYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (2.7 g, 24 mmol) was dissolved in 17 mL of anhydrous THF at rt. After 5 min glutaric anhydride (2.4 g, 21 mmol) was added and the resulting suspension stirred for 2 h at rt. The reaction mixture was then quenched with 20 mL of 1 M KHSO4, extracted with 50 mL of EtOAc, adjusted to pH 2–3 with 1 M KHSO4 and extracted twice with 50 mL EtOAc. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give a yellow oil which was purified by silica gel flash chromatography (eluent: EtOAc:Hexanes- 1:1) to give 1.65 g (35% yield) pure (TLC) 1-2.

Workup

  1. customThe reaction mixture was then quenched with 20 mL of 1 M KHSO4
  2. extractionextracted with 50 mL of EtOAc
  3. extractionextracted twice with 50 mL EtOAc
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil which
  8. customwas purified by silica gel flash chromatography (eluent: EtOAc:Hexanes- 1:1)
  9. customto give 1.65 g (35% yield) pure (TLC) 1-2

Sources & evidence

ORD record
ord-79d5abf0cd46408389bd0a6fd63523d9
Source dataset
uspto-grants-2007_06
Patent number
US07230005B2

Reaction notes

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