3,3-Dimethylglutaric anhydride → 5-(Tert-butoxy)-3,3-dimethyl-5-oxopentanoic acid

HRID 1110993Notes

Reaction equation

HRID 1110993 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.[CH3:11][C:12]([CH3:15])([O-:14])[CH3:13].[K+]>O1CCCC1>[C:12]([O:14][C:7](=[O:9])[CH2:8][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])([CH3:15])([CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 778133,3-Dimethylglutaric anhydrideHCID 23665647Potassium tert-butoxide

Product 1

HCID 156312555-(Tert-butoxy)-3,3-dimethyl-5-oxopentanoic acidYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,3-Dimethylglutaric anhydride (455 mg, 3.2 mmol) in tetrahydrofuran (THF, 5 mL) was treated with sublimed potassium t-butoxide (395 mg, 3.5 mmol). After 30 min the solution was concentrated, poured into saturated NaHCO3 solution and washed with ether. The aqueous phase was acidified to pH 4 with 0.5M H3PO4 and extracted with chloroform which was dried over Na2SO4 and evaporated to afford 179 mg (26%) of the desired product as an oil. NMR (300 MHz, CDCl3, ppm), 1.13 (s, 6H), 1.47 (s, 9H), 2.33 (s, 2H), 2.45 (s, 2H).

Workup

  1. concentrationAfter 30 min the solution was concentrated
  2. additionpoured into saturated NaHCO3 solution
  3. washwashed with ether
  4. extractionextracted with chloroform which
  5. dry with materialwas dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-ba2bf6d126cf4716adbce3409785c8c0
Source dataset
uspto-grants-1990_12
Patent number
US04977277

Reaction notes

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