Allyl bromide → Ethyl allyl(2,2-dimethoxyethyl)carbamate

HRID 1842704Notes

Reaction equation

HRID 1842704 reaction equation
[OH-].[K+].[CH3:3][O:4][CH:5]([O:13][CH3:14])[CH2:6][NH:7][C:8](=[O:12])[O:9][CH2:10][CH3:11].[CH2:15](Br)[CH:16]=[CH2:17]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH3:14][O:13][CH:5]([O:4][CH3:3])[CH2:6][N:7]([CH2:17][CH:16]=[CH2:15])[C:8](=[O:12])[O:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 10921057Ethyl 2,2-dimethoxyethylcarbamate2×

Product 1

HCID 10943907Ethyl allyl(2,2-dimethoxyethyl)carbamateYield 127.4%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

Crushed KOH (1417 g, 25.3 mol) was added in portions to a solution of ethyl N-(2,2-dimeth-oxyethyl)carbamate (Intermediate 43, 1123 g, 6.3 mol) in toluene (5 L). Benzyltriethyl-ammonium chloride (14.0 g, 0.06 mol) and allyl bromide (532 g, 4.4 mol) were then added at r.t. The mixture was then stirred at r.t. overnight. The mixture was then filtered and the reaction mixture was washed with brine (2 L), dried (Na2SO4) and concentrated in vacuo to give the title compound (1218 g, 89%) as a yellow oil; 1H NMR: (CDCl3) 1.23 (3H, s), 3.28 (2H, s), 3.36 (6H, s), 3.92 (2H, d), 4.12 (2H, s), 4.47 (1H, d), 5.08 (2H, d), 5.73 (1H, s).

Workup

  1. filtrationThe mixture was then filtered
  2. washthe reaction mixture was washed with brine (2 L)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-845b196dd91f47ef9768f19f627c2b8b
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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