3,4-dihydro-2H-pyran → 2-Fluoro-6-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde

HRID 1798045Notes

Reaction equation

HRID 1798045 reaction equation
[F: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>[F: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 220104032-Fluoro-4,6-dihydroxybenzaldehyde

Product 1

HCID 866539702-Fluoro-6-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehydeYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-fluoro-4,6-dihydroxybenzaldehyde (3.12 g, 20.0 mmol) and PPTS (0.51 g, 2.0 mmol) in dichloromethane (100 mL) was added dropwise DHP (3.02 g, 36.0 mmol). The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc/PE=1/15) on silica gel to give the title compounds as a colorless oil (3.99 g, Yield: 83.2%). MS (ESI) m/z=241 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-c98bac793a7c489999f2b3cb59e9c83d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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