3,4-dihydro-2H-pyran → HCID 86653968, compound

HRID 1798027Notes

Reaction equation

HRID 1798027 reaction equation
[CH2:1]([C:3]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([OH:12])[C:4]=1[CH:5]=[O:6])[CH3:2].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>ClCCl>[CH2:1]([C:3]1[CH:10]=[C:9]([O:11][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[CH:8]=[C:7]([OH:12])[C:4]=1[CH:5]=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 579397332-Ethyl-4,6-dihydroxybenzaldehyde

Product 1

HCID 86653968HCID 86653968, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-ethyl-4,6-dihydroxy-benzaldehyde (1 g, 6.02 mmol) in dichloromethane (50 mL) was added 3,4-dihydro-2H-pyran (1.1 mL, 12.05 mmol) and pyridium p-toluenesulfonic acid (0.010 g) at room temperature. The resulting mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2-ethyl-6-hydroxy-4-(tetrahydro-pyran-2-yloxy)-benzaldehyde (1.56 g, 100%). 1H NMR (400 MHz, CDCl3δ 12.40 (s, 1H), 10.08 (s, 1H), 6.48 (s, 1H), 6.40 (s, 1H), 5.50 (m, 1H), 3.84 (m, 1H), 3.60 (m, 1H), 2.90 (m, 2H), 2.00-1.50 (m, 6H), 1.30 (m, 3H).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-074590537ed04774920b14c64a33a62b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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