3,4-dihydro-2H-pyran → HCID 67296888, compound

HRID 1969393Notes

Reaction equation

HRID 1969393 reaction equation
[OH:1][CH:2]1[CH2:6][O:5][C:4](=[O:7])[CH2:3]1.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C(Cl)Cl>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:1][CH:2]1[CH2:6][O:5][C:4](=[O:7])[CH2:3]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 956523,4-Dihydroxybutanoic acid gamma-lactoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 67296888HCID 67296888, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-hydroxy-dihydrofuran-2(3H)-one (10 g, 0.1 mol, Alfa) and dihydropyran (12.5 g, 0.15 mol, Alfa) in 250 mL of dry CH2Cl2 was added PPTS (2.5 g 0.01 mol), and the reaction mixture was stirred at rt overnight. The reaction mixture was washed with brine and extracted with CH2Cl2 (100 mL×3), and the combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (3:1 (v/v) EtOAc/n-Hexane) to give the title compound as colorless oil (15.6 g, 68%).

Workup

  1. washThe reaction mixture was washed with brine
  2. extractionextracted with CH2Cl2 (100 mL×3)
  3. dry with materialthe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (3:1 (v/v) EtOAc/n-Hexane)

Sources & evidence

ORD record
ord-5820dce2e427433da43ca2d11a353c00
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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