Methyl 3,5-diethoxy-4-methoxybenzoate → HCID 68698382, compound

HRID 1990885Notes

Reaction equation

HRID 1990885 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]([O:13][CH3:14])=[C:6]([O:15][CH2:16][CH3:17])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:16]([O:15][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([O:10][CH2:11][CH3:12])[C:7]=1[O:13][CH3:14])[CH3:17]

Participants

4

Reactant 2

HCID 20095711Methyl 3,5-diethoxy-4-methoxybenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 68698382HCID 68698382, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-diethoxy-4-methoxy-benzoic acid methyl ester (0.34 g, 1.34 mmol, 1.0 equiv; prepared as described in EP 0 419 905 B1, Eisai Co.) in anhydrous THF (5 mL) was added lithium aluminium hydride (0.15 g, 4.01 mmol, 3.0 equiv) and the reaction mixture stirred at rt for 4 h. The crude reaction mixture was filtered over Hyflo Super Cel, the filtrate extracted with diethyl ether (3×50 mL) and the combined organic phases dried over MgSO4 providing 0.26 g (86%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.36 (t, J=7.0 Hz, 6H), 3.77 (s, 3H), 4.02 (q, J=7.0 Hz, 4H), 4.53 (s, 2H), 6.51 (s, 2H). MS (EI): 227.3 [M]+.

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered over Hyflo Super Cel
  3. extractionthe filtrate extracted with diethyl ether (3×50 mL)
  4. dry with materialthe combined organic phases dried over MgSO4 providing 0.26 g (86%) of the title compound

Sources & evidence

ORD record
ord-9b4e5dcd64ec4d6fb026e83c8fbe29c0
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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