Triethylamine → Methyl 3-ethoxy-2-(ethoxyimino)-3-iminopropanoate

HRID 647113

Reaction equation

HRID 647113 reaction equation
F[B-](F)(F)F.[CH2:6]([O+](CC)CC)[CH3:7].[F-].[C:14]([C:17](=[N:22][O:23][CH2:24][CH3:25])[C:18]([O:20][CH3:21])=[O:19])(=[O:16])[NH2:15].C(N(CC)CC)C>C(Cl)Cl.O>[NH:15]=[C:14]([O:16][CH2:6][CH3:7])[C:17](=[N:22][O:23][CH2:24][CH3:25])[C:18]([O:20][CH3:21])=[O:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 28179Fluoride IonHCID 2723982Triethyloxonium tetrafluoroborateHCID 53690437Methyl 3-amino-2-(ethoxyimino)-3-oxopropanoate

Product 1

HCID 53663360Methyl 3-ethoxy-2-(ethoxyimino)-3-iminopropanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Meerwein reagent (triethyloxonium tetrafluoroborate) {prepared from bron fluoride etherate (2.84 g) by a method of Org. Syn., 46, 113 (1966)} in methylene chloride (30 ml) was added methyl 2-carbamoyl-2-ethoxyiminoacetate (syn isomer, 2.6 g) and the mixture was stirred for 18 hours at room temperature. The reaction mixture was cooled in an ice-bath and triethylamine (3 g) was added thereto, followed by an addition of water (20 ml). The organic layer was separated out, dried over magnesium sulfate and evaporated to give crude methyl 3-imino-3-ethoxy-2-ethoxyiminopropionate (syn isomer) (5.0 g) as an oil. ##STR15##

Workup

  1. temperatureThe reaction mixture was cooled in an ice-bath
  2. customThe organic layer was separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c2c14045175f4522914e930aa28b5372
Source dataset
uspto-grants-1983_10
Patent number
US04407798

Linked notes

Loading…