Sodium Hydroxide → HCID 68534647, compound

HRID 1992861Notes

Reaction equation

HRID 1992861 reaction equation
[CH3:1][CH:2]([CH3:19])[CH:3]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:4][C:5]([O:7]CC)=[O:6].[OH-].[Na+]>C1COCC1.CCO>[CH3:1][CH:2]([CH3:19])[CH:3]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH2:4][C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68536371HCID 68536371, compound

Product 1

HCID 68534647HCID 68534647, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 4-methyl-3-{[3-(methyloxy)phenyl]methyl}pentanoate (66) (1.72 g, 6.51 mmol) was dissolved in THF (30 mL) and EtOH (30 mL). To this solution was added 1 N NaOH (35 mL). The reaction mixture was heated at 60° C. for 1.5 h. Cooled, the mixture was extracted with EtOAc. The combined extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give 1.54 g (100%) of the crude product 67 as a yellow oil. The crude product was used without further purification. 1H NMR (400 MHz, CDCl3): δ 0.91 (d, J=6.9 Hz, 3H), 0.94 (d, J=6.7 Hz, 3H), 1.70-1.80 (m, 1H), 2.10-2.25 (m, 2H), 2.32 (dd, J1=15.3 Hz, J2=6.5 Hz, 1H), 2.46 (dd, J1=13.7 Hz, J2=8.2 Hz, 1H), 2.67 (dd, J1=13.7 Hz, J2=6.4 Hz, 1H), 3.79 (s, 3H), 6.70-6.80 (m, 3H), 7.15-7.25 (m, 1H).

Workup

  1. temperatureCooled
  2. extractionthe mixture was extracted with EtOAc
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2f03de0ee15a45a3b99087be59387b1b
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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