Benzaldehyde → 3-(Benzylideneamino)dihydrofuran-2(3H)-one

HRID 247176

Reaction equation

HRID 247176 reaction equation
Br.[NH2:2][CH:3]1[CH2:8][CH2:7][O:6][C:4]1=[O:5].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2]>ClCCl>[CH:9](=[N:2][CH:3]1[CH2:8][CH2:7][O:6][C:4]1=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 73508Homoserine lactone hydrobromide

Product 1

HCID 140831233-(Benzylideneamino)dihydrofuran-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3.84 g of α-amino-γ-butyrolactone hydrogenbromide in 40 ml of dichloromethane is added 2.15 ml of benzaldehyde, followed by5.9 ml of triethylamine and excess magnesium sulfate. After stirring at room temperature for 20 hours, the mixture is filtered and the filtrate concentrated. A 200 ml portion of ether is added and the resulting suspension filtered. The filtrate is washed with 50 ml of saturated aqueous sodium chloride. The aqueous phase is extracted with two 100 ml portions of ether. The combined organic phase is dried (magnesium sulfate), filtered, and then concentrated. The residue is evaporatively distilled at 0.05 mmHg (Krugelrohr oven 200°-250° C.) to give 3.5 g of N-benzylidene-α-amino-γ-butyrolactone as an oil which solidifies on storage in a freezer:

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate concentrated
  3. additionA 200 ml portion of ether is added
  4. filtrationthe resulting suspension filtered
  5. washThe filtrate is washed with 50 ml of saturated aqueous sodium chloride
  6. extractionThe aqueous phase is extracted with two 100 ml portions of ether
  7. dry with materialThe combined organic phase is dried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. distillationThe residue is evaporatively distilled at 0.05 mmHg (Krugelrohr oven 200°-250° C.)

Sources & evidence

ORD record
ord-97ec6b88068f4390900188ddec71c939
Source dataset
uspto-grants-1987_11
Patent number
US04705846

Linked notes

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