3,4-dihydro-2H-pyran → HCID 17985424, compound

HRID 557186Notes

Reaction equation

HRID 557186 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([OH:11])[CH:3]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1>ClCCl>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([O:11][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][O:29]2)[CH:3]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 17985866HCID 17985866, compound

Product 1

HCID 17985424HCID 17985424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

Combine 7-bromo-5-hydroxybenzofuran (5.0 g, 0.0235 mol) with pyridinium para-toluenesulfonate (0.59 g, 0.1 equivalent) and dissolve in 60 mL dichloromethane under nitrogen. Add via syringe 3,4-dihydro-2H-pyran (3.2 mL, 1.5 equivalents) and stir at 20° C. overnight. Dilute with dichloromethane then extract with 1N sodium hydroxide and wash with brine. Dry over sodium sulfate, filtered, and then concentrate to afford the title compound as a brown oil.

Workup

  1. extractionthen extract with 1N sodium hydroxide
  2. washwash with brine
  3. dry with materialDry over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-1cde466f39b1429281cc6946b339c1b9
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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