Tetrahydrofuran → HCID 13583743, compound

HRID 892473Notes

Reaction equation

HRID 892473 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].C([CH:23]([C:27](Cl)=[O:28])[C:24](Cl)=[O:25])C.[O:30]1CC[CH2:32][CH2:31]1>C(OCC)C.O>[CH2:31]([O:30][C:27]([CH2:23][C:24]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:25])=[O:28])[CH3:32]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 80908N-Benzylglycine ethyl esterHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 13583743HCID 13583743, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a 0° C. solution of ethyl N-benzylglycinate (8 g) in tetrahydrofuran (4 ml) and diethyl ether (42 ml) was added simultaneously a solution of K2CO3 (5.72 g) in 20 ml of water and ethyl malonylchloride (6.54 g) in 20 ml diethyl ether. Following the addition the mixture was stirred at 0° for 1 hour then warmed to ambient temperature with stirring for 2 hours. The layers were separated with the organic phase washed once with brine. After drying (Na2SO4) and concentrating, there was obtained 12.5 g (98.8%) of the product as a viscous oil.

Workup

  1. additionthe addition the mixture
  2. stirringwith stirring for 2 hours
  3. customThe layers were separated with the organic phase
  4. washwashed once with brine
  5. dry with materialAfter drying (Na2SO4)
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-e227ef23d64642509ed382621f57c992
Source dataset
uspto-grants-1992_06
Patent number
US05118688

Reaction notes

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