3,4-dihydro-2H-pyran → HCID 22137302, compound

HRID 1827518Notes

Reaction equation

HRID 1827518 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH3:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 22137302HCID 22137302, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-methylbenzaldehyde (3.0 g, 22.03 mmol) in 45 mL methylene chloride was added 3,4-dihydro-2H-pyran (5.0 mL, 54.8 mmol) and pyridinium p-toluenesulfonate (0.55 g, 2.19 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between methylene chloride and saturated aqueous sodium bicarbonate. The layers were separated and the aqueous layer was extracted with three portions of methylene chloride. The combined organic layers were washed with saturated aqueous sodium chloride, dried (sodium sulfate), filtered, and concentrated. Silica gel flash chromatography of the residue (10% ether/hexanes to 20% ether/hexanes) afforded 4.35 g of the title compound of Step A. MS 221.1 (M+1)+

Workup

  1. customThe reaction mixture was partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with three portions of methylene chloride
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4e15f7a7a76842ba8dc3ddb5b850502b
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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