Water → HCID 6032635, compound

HRID 1994158Notes

Reaction equation

HRID 1994158 reaction equation
C([O:3][C:4](=[O:17])/[C:5](=[CH:8]/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)/[CH2:6][CH3:7])C.[Li+].[OH-].O>C1COCC1.CCOC(C)=O.Cl>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)/[CH:8]=[C:5](\[CH2:6][CH3:7])/[C:4]([OH:17])=[O:3]

Participants

7

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58674435HCID 58674435, compound

Product 1

HCID 6032635HCID 6032635, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-Ethyl-2-(3-methoxybenzylidene)butanoate (300 mg, 1.28 mmol) was dissolved in THF (30 mL), and LiOH (61 mg, 2.56 mmol), and water (100 μL) were added. The reaction mixture was heated to reflux for 48 h and then cooled to rt. The reaction mixture was diluted with EtOAc and 1N HCl. The aqueous phase was extracted with EtOAc and the combined organic solutions were dried over Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, 0-70% EtOAc with 1% acetic acid in DCM) provided the title compound (190 mg). 1H NMR (400 MHz, d6-DMSO): δ 7.52 (s, 1H), 7.37-7.33 (dd, 1H), 6.99 (d, 1H), 6.95-6.93 (m, 2H), 3.77 (s, 3H), 2.43 (q, 2H), and 1.10 (t, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 48 h
  3. extractionThe aqueous phase was extracted with EtOAc
  4. dry with materialthe combined organic solutions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography (SiO2, 0-70% EtOAc with 1% acetic acid in DCM)

Sources & evidence

ORD record
ord-ea14641e61e840109780c49cf4a46c3a
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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