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

HRID 585570Notes

Reaction equation

HRID 585570 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]([O-:15])([CH3:14])[CH3:13].[K+]>C1COCC1.CCOCC>[C:12]([O:15][C:7](=[O:9])[CH2:8][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 2

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

Product 1

HCID 156312555-(Tert-butoxy)-3,3-dimethyl-5-oxopentanoic acidYield 69%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3,3-Dimethylglutaric anhydride (6.5 g, 45.7 mmol) was dissolved in THF (75 mL) and the t-BuOK, 1M in THF (52.5 mL, 52.5 mmol) was added and the mixture was stirred at room temperature for one hour. The reaction mixture was then diluted with ether, washed with 1N HCl, brine (3×), dried (MgSO4), and concentrated to give 6.8 g (69%) of the desired product as a colorless oil. 1H NMR (DMSO-d6) 12.0 (br s, 1H), 2.22 (s, 4H), 1.39 (s, 9H), 1.03 (s, 6H).

Workup

  1. washwashed with 1N HCl, brine (3×)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2aee5543b05c48408ac26fed18e5fd92
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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