Benzaldehyde → HCID 11731822, compound

HRID 2227900Notes

Reaction equation

HRID 2227900 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-trimethylsilyl triflate were added to the solution and the mixture was reacted under stirring for one hour. After the temperature of the mixture was raised up to 0° C., 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 to obtain 184 mg (0.476 mmol) of 3-diphenylmethyl-4-methoxycarbonyl-5-phenyl-2-oxzolidinone as white crystal. (Yield based on 3-diphenylmethyl-5-methoxy-2(3H)oxazolone: 95%.) According to HPLC analysis, a formation ratio of cis/trans-isomers of the formed product was 5/95.

Workup

  1. additionwere added to the solution
  2. customthe mixture was reacted
  3. additionwas added to the resulting reaction mixture
  4. extractionthe mixture was extracted with 20 ml of methylene chloride
  5. washThe organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain 184 mg (0.476 mmol) of 3-diphenylmethyl-4-methoxycarbonyl-5-phenyl-2-oxzolidinone as white crystal
  9. custom(Yield based on 3-diphenylmethyl-5-methoxy-2(3H)oxazolone: 95%.)

Sources & evidence

ORD record
ord-ce3e7e053f2f4bb3b69a65d30f4b276b
Source dataset
uspto-grants-2002_07
Patent number
US06414160B1

Reaction notes

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