Tetrahydrofuran → HCID 2968453, compound

HRID 391231Notes

Reaction equation

HRID 391231 reaction equation
O1CCCC1.[C:6]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.[CH2:24]([O:26][C:27](=[O:31])[C:28](Cl)=[O:29])[CH3:25]>C(OCC)(=O)C.O>[CH2:24]([O:26][C:27](=[O:31])[C:28]([NH:14][C:13]1[CH:12]=[CH:11][C:10]([C:6]([CH3:9])([CH3:7])[CH3:8])=[CH:16][CH:15]=1)=[O:29])[CH3:25]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 698614-Tert-Butylaniline

Product 1

HCID 2968453HCID 2968453, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 20 ml of tetrahydrofuran, were added 3.13 g of 4-t-butyl aniline, and 2.42 g of triethylamine, and the solution was iced. In the iced solution, 2.73 g of ethyl chloroglyoxylic acid was added dropwise to the resulting solution over 10 minutes, after which the solution was heated to room temperature, and stirred for about one hour. After completion of the reaction, 50 ml of water was added to the reacted solution, and extraction was carried out three times with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and solvent was evaporated under reduced pressure to obtain 4.97 g (99.7%) of ethyl-2-(4-t-butylphenylamino)-2-oxoacetate.

Workup

  1. additionwas added to the reacted solution, and extraction
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate and solvent
  3. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-0126cc8d43d44d55a9c0c9342ed9b5b5
Source dataset
uspto-grants-2013_02
Patent number
US08383829B2

Reaction notes

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