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

HRID 1798072Notes

Reaction equation

HRID 1798072 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].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>ClCCl>[Br: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]([OH:11])[C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 58292554HCID 58292554, compound

Product 1

HCID 58292840HCID 58292840, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-bromo-4,6-dihydroxybenzaldehyde (2.50 g, 11.5 mmol) in dichloromethane was added 3,4-dihydro-2H-pyran (1.45 g, 17.3 mol) and PPTs (0.58 g, 2.3 mmol) at room temperature. The resulting mixture was stirred for 2 h and quenched by saturated aqueous NaHCO3 (35 mL). The organic layer was washed with water (20 mL), brine (20 mL) and dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (PE:EtOAc=2:1) on silica gel to afford the title compound as a colorless oil (2.93 g, yield: 85%)

Workup

  1. customquenched by saturated aqueous NaHCO3 (35 mL)
  2. washThe organic layer was washed with water (20 mL), brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (PE:EtOAc=2:1) on silica gel

Sources & evidence

ORD record
ord-1326a0ffb9a54aac98c4edee4c70a3fc
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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