3,4-dihydro-2H-pyran → HCID 58292840, compound

HRID 1798065Notes

Reaction equation

HRID 1798065 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[CH2:29]1[CH2:34][O:33][CH:32]=[CH:31][CH2:30]1>ClCCl>[Br:1][C:2]1[CH:9]=[C:8]([O:10][CH:32]2[CH2:31][CH2:30][CH2:29][CH2:34][O:33]2)[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 58292554HCID 58292554, compound

Product 1

HCID 58292840HCID 58292840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-4,6-dihydroxybenzaldehyde (4.34 g, 20.0 mmol) and PPTS (0.51 g, 2.0 mmol) in dichloromethane (100 mL) was added DHP (3.02 g, 36.0 mmol). The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/15) on silica gel to give the title compound as a colorless oil. (4.52 g, Y: 75.1%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (EtOAc/PE=1/15) on silica gel

Sources & evidence

ORD record
ord-728c680ed5bc4a2f82fd8f0969e04973
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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