3,4-dihydro-2H-pyran → HCID 10823699, compound

HRID 1798031Notes

Reaction equation

HRID 1798031 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>ClCCl>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[CH:7]=[C:6]([CH3:11])[C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 251690o-Orsellinaldehyde

Product 1

HCID 10823699HCID 10823699, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,4-dihydroxy-6-methyl-benzaldehyde (6.37 g, 37.88 mmol) in dichloromethane (150 mL) was added 3,4-dihydro-2H-pyran (4.78 g, 56.82 mmol) and pyridium p-toluenesulfonic acid (1.90 g, 7.58 mmol) at room temperature. The resulting mixture was stirred at room temperature for 18 hours then quenched by adding saturated NaHCO3 at 0° C. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (EtOAc/hexane=1:3) to give pure product (8.78 g, 98.1%). 1H NMR (400 MHz, CDCl3) δ ppm 12.33 (s, 1H), 10.11 (s, 1H), 6.47 (s, 1H), 6.39 (s, 1H), 5.49 (t, J=3.13 Hz, 1H), 3.78-3.90 (m, 1H), 3.52-3.72 (m, 1H), 2.54 (s, 3H), 1.77-2.03 (m, 3H), 1.53-1.70 (m, 3H); MS (ESI) m/z=285 [M+H]+.

Workup

  1. customthen quenched
  2. additionby adding saturated NaHCO3 at 0° C
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash column chromatography (EtOAc/hexane=1:3)

Sources & evidence

ORD record
ord-7b9605b9f7384a299fe607637980876b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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