Hydrochloric Acid → Ethyl 2-(3-methoxy-6,6-dimethyl-2-oxocyclohex-3-en-1-yl)-2-oxoacetate

HRID 44586Notes

Reaction equation

HRID 44586 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6](=[O:13])[CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][CH:10]=1.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>O1CCCC1.O>[CH3:3][O:4][C:5]1[C:6](=[O:13])[CH:7]([C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]([CH3:11])([CH3:12])[CH2:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 552979862-Methoxy-5,5-dimethylcyclohex-2-enone

Product 1

HCID 57444091Ethyl 2-(3-methoxy-6,6-dimethyl-2-oxocyclohex-3-en-1-yl)-2-oxoacetateYield 2,084.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

60% sodium hydride in mineral oil (2.41 g, 60.3 mmol) was suspended in anhydrous tetrahydrofuran (60 mL) under argon atmosphere and treated with a solution of 2-methoxy-5,5-dimethyl-cyclohex-2-enone (6.20 g, 40:2 mmol) in anhydrous tetrahydrofuran (50 mL). After 15 minutes, a solution of diethyl oxalate (8.17 mL, 60.3 mmol) in anhydrous tetrahydrofuran (50 mL) was added and the mixture was refluxed for 1 hour. The slurry was diluted with water (800 mL), acidified with 1N HCl (50 mL) and extracted with ethyl acetate (500 mL×2). The organic layers were collected, washed with brine, dried on Na2SO4 and evaporated to dryness to obtain the crude title compound (10.60 g) as an orange oil, which was used without further purification.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. extractionextracted with ethyl acetate (500 mL×2)
  3. customThe organic layers were collected
  4. washwashed with brine
  5. customdried on Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-461c861174624b48ab901099601b860d
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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