Benzaldehyde → 2-Phenyl-2H-pyran-4(3H)-one

HRID 650697Notes

Reaction equation

HRID 650697 reaction equation
ClCCl.[CH:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CO[CH:14]=[CH:15][C:16]([O:18][Si](C)(C)C)=[CH2:17]>FC(F)(F)C(O)=O.N1C=CC=CC=1.O>[C:5]1([CH:4]2[CH2:17][C:16](=[O:18])[CH:15]=[CH:14][O:11]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 6344DichloromethaneHCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadiene

Product 1

HCID 5690202-Phenyl-2H-pyran-4(3H)-oneYield 93%

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 6422Trifluoroacetic acidCatalystHCID 962WaterSolvent

Procedure

To a round flask of 5 ml having a magnet stirrer put therein, 19.1 mg (0.01 mmol) of the catalyst (tetrahydrate) obtained in Example 8 and 1 ml of dichloromethane were added for dissolution, then benzaldehyde (10 μl, 0.1 mmol) and 1-methoxy-3-trimethylsilyloxy-1,3-butadiene (purity: 90%, 30.0 μl, 0.150 mmol) were added thereto, and the reaction was carried out at room temperature for 24 hours. After the reaction had been completed, two drops of trifluoroacetic acid was added by a microsyringe, three drops of pyridine was added by a microsyringe, and 1 ml of water was added. Successively, extraction with dichloromethane, drying over anhydrous magnesium sulfate, concentration and purification by preparative silica gel column chromatography (hexane/ethyl acetate=4/1) were carried out to obtain 16.1 mg of the desired compound (R)-2-phenyl-2,3-dihydro-4H-pyran-4-one. As a result of analysis, the yield was 93% and the optical purity was 19% (R).

Workup

  1. customTo a round flask of 5 ml having
  2. customa magnet stirrer put
  3. additionwere added for dissolution
  4. additionwas added
  5. extractionSuccessively, extraction with dichloromethane
  6. dry with materialdrying over anhydrous magnesium sulfate, concentration and purification by preparative silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-6d0477b2e22a4c7bbae98a7f9dc9bc0a
Source dataset
uspto-grants-2001_08
Patent number
US06274745B1

Reaction notes

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