Ethyl isobutyrate → HCID 11009344, compound

HRID 1469146Notes

Reaction equation

HRID 1469146 reaction equation
[Li+].CC([N-]C(C)C)C.C1COCC1.C(C1C=CC=CC=1)C.CCCCCCC.[CH3:29][CH:30]([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32].[C:37]1(=[O:43])[O:42][C:40](=[O:41])[CH2:39][CH2:38]1.C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C.O>[CH2:34]([O:33][C:31](=[O:32])[C:30]([CH3:36])([CH3:29])[C:40](=[O:41])[CH2:39][CH2:38][C:37]([OH:42])=[O:43])[CH3:35]

Participants

8

Reactant 4

HCID 7342Ethyl isobutyrateHCID 7922Succinic anhydrideHCID 516892Sodium BicarbonateHCID 86590273LDA THF ethylbenzene heptane

Product 1

HCID 11009344HCID 11009344, compoundYield 68.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To dehydrated THF (20 mL) was added a 2.0M LDA/THF-ethylbenzene-heptane solution (7.88 mL), this was cooled to around −78° C. in a dry ice-methanol bath, and a solution of ethyl 2-methylpropanoate (1.74 g) in dehydrated THF (5 mL) was slowly added dropwise. After the mixture was stirred at around −78° C. for 1 hour, this solution was added dropwise to a suspension of succinic acid anhydride (1.50 g) in dehydrated THF (5 mL) over 5 minutes under an ice bath. After stirred at the same temperature for 40 minutes, the mixture was stirred at room temperature for 3 hours. Into the reaction solution was slowly placed water under an ice bath, ethyl acetate and an aqueous saturated sodium bicarbonate solution were added, followed by extraction. To the resulting aqueous phase was added 1N hydrochloric acid to adjust a pH at around 3, followed by extraction with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was washed with dichloromethane, a compound derived from succinic acid anhydride was removed by filtration, and the resulting filtrate was concentrated under reduced pressure to obtain the title compound (2.22 g) having the following physical property values.

Workup

  1. stirringAfter stirred at the same temperature for 40 minutes
  2. stirringthe mixture was stirred at room temperature for 3 hours
  3. extractionfollowed by extraction
  4. additionTo the resulting aqueous phase was added 1N hydrochloric acid
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting crude product was washed with dichloromethane
  9. customwas removed by filtration
  10. concentrationthe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eee9662b4e364aedae13328686cecb8a
Source dataset
uspto-grants-2015_04
Patent number
US09006246B2

Reaction notes

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