2,5-Dimethoxytetrahydrofuran → HCID 53649664, compound

HRID 275647Notes

Reaction equation

HRID 275647 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH2:7][C:8]([NH:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].CO[CH:31]1[CH2:35][CH2:34][CH:33](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([NH:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])=[CH:22][CH:23]=2)[CH:31]=[CH:35][CH:34]=[CH:33]1

Participants

5

Reactant 3

HCID 790982,5-DimethoxytetrahydrofuranHCID 517045Sodium AcetateHCID 53821646HCID 53821646, compound

Product 1

HCID 53649664HCID 53649664, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

4,6 g of diethyl 4-aminobenzylacetamidomalonate in 104 ml of acetic acid are placed in a three-necked flask which is maintained under nitrogen. 7.02 g of sodium acetate are added, followed by 1.87 ml of 2,5-dimethoxytetrahydrofuran. The mixture is heated at 65° C. for 1 h 15 min, then cooled down and extracted with 100 ml of dichloromethane and 100 ml of distilled water. The aqueous phase is separated off after settling and then washed with 3 times 100 ml of dichloromethane. The organic phases are combined, washed with 100 ml of water and then with 100 ml of a saturated solution of NaCl, separated off after settling and then dried over magnesium sulphate; the phases are filtered and then evaporated to dryness under reduced pressure (50 kPa) in order to yield 6.2 g of a solid which is purified by flash chromatography (eluent CH2Cl2/acetone 75/25 by volume). This results in 3.57 g of diethyl 4-(1-pyrrolyl)benzylacetamidomalonate in the form of a beige solid which melts at 110° C.

Workup

  1. temperaturewhich is maintained under nitrogen
  2. temperaturecooled down
  3. extractionextracted with 100 ml of dichloromethane and 100 ml of distilled water
  4. customThe aqueous phase is separated off
  5. washwashed with 3 times 100 ml of dichloromethane
  6. washwashed with 100 ml of water
  7. customwith 100 ml of a saturated solution of NaCl, separated off
  8. dry with materialdried over magnesium sulphate
  9. filtrationthe phases are filtered
  10. customevaporated to dryness under reduced pressure (50 kPa) in order

Sources & evidence

ORD record
ord-4abb63068c0a4f0a818134184308a10e
Source dataset
uspto-grants-2002_03
Patent number
US06352839B1

Reaction notes

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