3,4-dihydro-2H-pyran → 2-Methoxy-4-[(oxan-2-yl)oxy]benzaldehyde

HRID 1827516Notes

Reaction equation

HRID 1827516 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 40482782-Methoxy-4-[(oxan-2-yl)oxy]benzaldehydeYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-4-hydroxy-benzaldehyde (2.40 g, 15.8 mmol) and 3,4-dihydro-2H-pyran (3.6 mL, 39.5 mmol) in 50 mL methylene chloride was added pyridinium p-toluenesulfonate (0.397 g, 1.58 mmol). The reaction mixture was stirred at room temperature overnight at which time the reaction was concentrated to one-half its original volume. The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate and water. The organic layer was dried (magnesium sulfate), filtered, and concentrated. Medium pressure silica gel chromatography of the residue (5% ethyl acetate/hexanes) afforded 2.13 g (58%) of the title compound of Step A. MS 152.9 (M+1-THP)+

Workup

  1. concentrationwas concentrated to one-half its original volume
  2. customThe layers were separated
  3. washthe organic layer was washed with saturated aqueous sodium bicarbonate and water
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4308a77f03544a698f5d24e338b4d9f6
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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