Tetrahydrofuran → HCID 14209149, compound

HRID 279778Notes

Reaction equation

HRID 279778 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[CH2:8][CH:7]1[C:11](O)=O.C(N(CC)CC)C.[N+](=C)=[N-].[N+](=CC(C1N(CC2C=CC(OC)=CC=2OC)[C:37](=[O:50])C1)=O)=[N-].[O:51]1CCCC1>C(OCC)C>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[CH2:8][CH:7]1[CH2:11][C:37]([OH:50])=[O:51]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9550DiazomethaneHCID 14209146HCID 14209146, compoundHCID 54501513HCID 54501513, compound

Product 1

HCID 14209149HCID 14209149, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-15 °C

Procedure

13.2 g (50 millimoles) of 1-(2,4-dimethoxy-benzyl)-4-oxo-2-azetidine-carboxylic acid prepared according to the preceding paragraph are dissolved in 150 ml of anhydrous tetrahydrofurane and to the solution first 7.3 ml (52.5 millimole) of triethylamine and thereafter under stirring and ice-cooling 5.0 ml (52.5 millimoles) of ethylchloroformiate are added. The mixture is cooled to -15° C., stirred at this temperature for 20 minutes and the precipitated triethylamine salt is filtered off under argon. To the filtrate a solution of 22.5 g (150 millimole) diazomethane and 230 ml of cold diethyl ether is added. The solution is stirred, allowed to warm to ambient temperature and after 2 hours the mixture is evaporated to dryness. The residue is dissolved in 20 ml of benzene and subjected to column chromatography (adsorbent: 150 g of Kieselgel G, diameter 0.063-0.2000 mm; eluant: benzene-acetone 7:2). On rubbing with ether a crystalline product is obtained. Yield: 10.5 g (73%) of 4-diazoacetyl-1-(2,4-dimethoxy-benzyl)-2-azetidinone, m.p.: 90°-91° C.

Workup

  1. temperatureice-cooling 5.0 ml (52.5 millimoles) of ethylchloroformiate
  2. additionare added
  3. stirringstirred at this temperature for 20 minutes
  4. filtrationthe precipitated triethylamine salt is filtered off under argon
  5. stirringThe solution is stirred
  6. temperatureto warm to ambient temperature and after 2 hours the mixture
  7. customis evaporated to dryness
  8. dissolutionThe residue is dissolved in 20 ml of benzene
  9. customis obtained

Sources & evidence

ORD record
ord-89dfed38b0914e05b5df6165c7a8b419
Source dataset
uspto-grants-1986_05
Patent number
US04587049

Reaction notes

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