Benzaldehyde → HCID 11731822, compound

HRID 2227899Notes

Reaction equation

HRID 2227899 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH:12]=[C:11]([O:13][CH3:14])[O:10][C:9]2=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:8]2[CH:12]([C:11]([O:13][CH3:14])=[O:10])[CH:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:29][C:9]2=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 11808112HCID 11808112, compound

Product 1

HCID 11731822HCID 11731822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under argon atmosphere, in 3 ml of methylene chloride was dissolved 141 mg (0.5 mmol) of 3-diphenylmethyl-5-methoxy-2(3H)oxazolone, and after cooling the solution to −78° C., 53.1 mg (0.5 mmol) of benzaldehyde and 0.05 ml (0.05 mmol) of a methylene chloride solution containing 1.0 M-TiBr4 were added to the solution and the mixture was reacted under stirring for 2 hours. Then, the temperature of the mixture was raised to room temperature, and after stirring for further 16 hours, 15 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the resulting reaction mixture and the mixture was extracted with 20 ml of methylene chloride. The organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. When the resulting concentrated residue was quantitated by the HPLC method, yield of 3-diphenylmethyl-4-methoxycarbonyl-5-phenyl-2-oxzolidinone was 26%. A formation ratio of cis/trans-isomers of the formed product was 8/92.

Workup

  1. additionwere added to the solution
  2. customthe mixture was reacted
  3. temperatureThen, the temperature of the mixture was raised to room temperature
  4. stirringafter stirring for further 16 hours
  5. extractionthe mixture was extracted with 20 ml of methylene chloride
  6. washThe organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e7af68c4b10414686ffb520360ddc2a
Source dataset
uspto-grants-2002_07
Patent number
US06414160B1

Reaction notes

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