3,4-dihydro-2H-pyran → HCID 68457600, compound

HRID 501769Notes

Reaction equation

HRID 501769 reaction equation
[OH:1][C:2]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11](=[O:16])[CH2:10][CH2:9]2)=[O:5].[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:1][C:2]1[CH:20]=[C:19]([O:21][CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27][O:22]2)[CH:18]=[CH:17][C:3]=1[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11](=[O:16])[CH2:10][CH2:9]2)=[O:5]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 23021508HCID 23021508, compound

Product 1

HCID 68457600HCID 68457600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g of 6-(2,4-dihydroxybenzoyl)-2-chromanone was suspended in 100 mL of methylene chloride, to which 3.53 mL of 3,4-dihydro-2H-pyran and 0.884 g of pyridinium p-toluenesulfonate were added, and this mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate and the solvent was distilled out thereof under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1] to yield 6.99 g of 6-[2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)benzoyl]-2-chromanon as light yellow solid.

Workup

  1. additionwere added
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out thereof under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=3:1]

Sources & evidence

ORD record
ord-f60bf5e3d4ea42f28ec8a983d5cdb53d
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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