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

HRID 470208Notes

Reaction equation

HRID 470208 reaction equation
[CH3:1][O:2][CH:3]([O:16][CH3:17])[CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:22]([N:5]([CH2:4][CH:3]([O:2][CH3:1])[O:16][CH3:17])[C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:21]=[CH2:20]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 10800009Benzyl (2,2-dimethoxyethyl)carbamate

Product 1

HCID 11044136Benzyl allyl(2,2-dimethoxyethyl)carbamateYield 75.4%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of benzyl N-(2,2-dimethoxyethyl)carbamate (50 g, 208.9 mmol) in toluene (180 mL) is treated with solid potassium hydroxide (51.6 g, 919.69 mmol) under nitrogen. After 10 minutes, benzyltriethylammonium chloride (0.8 g, 3.1 mmol) is added. After another 10 minutes a solution of allyl bromide (33 g, 272.8 mmol) in toluene (50 mL) is added drop wise over 10 minutes. The resultant mixture is stirred at 50° C. for 48 hours. The mixture is cooled to room temperature and quenched with water. The organic layer is separated, washed with brine, dried over magnesium sulfate, and concentrated to dryness to give the title compound (44 g, 75%). ES/MS (m/e): 280 (M+H).

Workup

  1. customquenched with water
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-932f2a05e6eb4360ac4b17c4b1a21b38
Source dataset
uspto-grants-2014_01
Patent number
US08629270B2

Reaction notes

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