Aluminium lithium hydride → HCID 58706341, compound

HRID 1990820Notes

Reaction equation

HRID 1990820 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:7]=[C:6]([O:17][CH2:18][CH3:19])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.O=[Mn]=O>[CH2:18]([O:17][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:7]=1)[CH:3]=[O:2])[CH3:19]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68457750HCID 68457750, compound

Product 1

HCID 58706341HCID 58706341, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-ethoxy-5-(tetrahydro-pyran-4-yloxy)-benzoic acid methyl ester (0.64 g, 2.28 mmol, 1.0 equiv) in anhydrous THF (20 mL) was added lithium aluminium hydride (0.217 g, 5.71 mmol, 2.5 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 0.56 g (100%) of the benzyl alcohol. The crude reaction product (0.56 g, 2.22 mmol, 1.0 equiv) was dissolved in THF (20 mL) and activated MnO2 (1.93 g, 22.2 mmol, 10.0 equiv) was added. After stirring at rt for 3 h, the reaction mixture was filtered over Hyflo Super Cel and the solvent removed by evaporation under reduced pressure. A conc. solution of sodium chloride (100 mL) was added, the mixture extracted with ethyl acetate (3×100 mL) and the combined organic phases dried over MgSO4 providing 0.46 g (83%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.34 (t, J=7.0 Hz, 3H), 1.66-1.76 (m, 2H), 1.91-1.98 (m, 2H), 3.46-3.53 (m, 2H), 3.85-3.92 (m, 2H), 3.98 (q, J=7.0 Hz, 2H), 4.41-4.47 (m, 1H), 6.62-6.63 (m, 1H), 6.89-6.91 (m, 2H), 9.79 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.62, 31.67, 63.90, 64.96, 72.02, 107.96, 108.68, 109.44, 138.49, 158.85, 160.71, 191.72. MS (ISP): 251.1 [M+H]+.

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 0.56 g (100%) of the benzyl alcohol
  5. stirringAfter stirring at rt for 3 h
  6. filtrationthe reaction mixture was filtered over Hyflo Super Cel
  7. customthe solvent removed by evaporation under reduced pressure
  8. additionA conc. solution of sodium chloride (100 mL) was added
  9. extractionthe mixture extracted with ethyl acetate (3×100 mL)
  10. dry with materialthe combined organic phases dried over MgSO4 providing 0.46 g (83%) of the title compound

Sources & evidence

ORD record
ord-a38a27b78b6b4c489a80a236f557b0d9
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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