2,6-Lutidine → 3-(Tetrahydro-2-furanyl)phenylmethanol

HRID 991329Notes

Reaction equation

HRID 991329 reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].N1C(C)=CC=CC=1C.[H][H]>[Pd].C1COCC1>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH2:9][OH:10])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 219810903-(Dihydro-2-furanyl)benzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 235061043-(Tetrahydro-2-furanyl)phenylmethanolYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

EX-608C) A THF (15 mL) solution of the aldehyde from EX-608B (0.70 g, 4.0 mmol) and 2,6-lutidine (0.46 mL, 4.0 mmol) was stirred in a hydrogen atmosphere (50 psi) in the presence of 10% Pd/C (0.29 g) for 18 h at room temperature. The slurry was filtered through celite, and the solvent was removed. The residue was taken up in ethyl acetate and washed with 1 N HCl and brine. The organic layer was dried (MgSO4) and evaporated to give 0.50 g (70%) of the desired 3-(tetrahydro-2-furanyl)phenylmethanol product as a yellow oil. The formation of the desired product was monitored by the disappearance of the aldehyde (δ10) and olefin peaks in the 1H NMR spectrum.

Workup

  1. filtrationThe slurry was filtered through celite
  2. customthe solvent was removed
  3. washwashed with 1 N HCl and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-9ee3eded146c4b59a329a44dd5617dd5
Source dataset
uspto-grants-2002_10
Patent number
US06462092B1

Reaction notes

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