Potassium Hydroxide → Ethyl N-(2-buten-1-yl)-N-(2,2-dimethoxyethyl)-carbamate

HRID 1646020Notes

Reaction equation

HRID 1646020 reaction equation
[CH3:1][O:2][CH:3]([O:11][CH3:12])[CH2:4][NH:5][C:6](=[O:10])[O:7][CH2:8][CH3:9].[OH-].[K+].[CH2:15](Br)[CH:16]=[CH:17][CH3:18]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH2:15]([N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:11][CH3:12])[C:6](=[O:10])[O:7][CH2:8][CH3:9])[CH:16]=[CH:17][CH3:18]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 1224142-Butene, 1-bromo-HCID 10921057Ethyl 2,2-dimethoxyethylcarbamate

Product 1

HCID 54206204Ethyl N-(2-buten-1-yl)-N-(2,2-dimethoxyethyl)-carbamate

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Alternatively 90 g (0.5 mol) of ethyl N-(2,2-dimethoxyethyl)-carbamate are dissolved in 500 ml of toluene, 100 g of powdered potassium hydroxide and 1.5 g of triethylbenzylammonium chloride are added and 80 g (0.6 mol) of crotyl bromide (isomer mixture) are added dropwise. The mixture is stirred overnight at room temperature, the salts are dissolved in water, and the aqueous phase is separated off and extracted once using 100 ml of toluene. The extract is dried over potassium carbonate and concentrated, and the residue is distilled.

Workup

  1. customthe aqueous phase is separated off
  2. extractionextracted once
  3. dry with materialThe extract is dried over potassium carbonate
  4. concentrationconcentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-d2be9d6cc43c4f409aa2a24d1e8d301e
Source dataset
uspto-grants-1993_01
Patent number
US05177210

Reaction notes

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