3,4-dihydro-2H-pyran → HCID 66939482, compound

HRID 1257393Notes

Reaction equation

HRID 1257393 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][OH:15])[N:13]=2)[CH:6]=[CH:7][CH:8]=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:15][CH2:14][C:12]1[N:13]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:16])[F:17])[CH:4]=2)[S:10][CH:11]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 56706473HCID 56706473, compound

Product 1

HCID 66939482HCID 66939482, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

To a solution (50 mL) of the compound (7.0 g, 27 mmol) obtained in Example 64b in toluene were added dihydropyran (4.9 mL, 54 mmol) and conc. sulfuric acid (3 drops), and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20) to give the title compound (9.2 g, 99%) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-27c032fb96394b2d8c200def65e3c00f
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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