Propargyl bromide → Carbamic acid, [2-(2-propynyloxy)ethyl]-, 1,1-dimethylethyl ester (9CI)

HRID 2237365Notes

Reaction equation

HRID 2237365 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH2:14](Br)[C:15]#[CH:16]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][O:10][CH2:16][C:15]#[CH:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamate

Product 1

HCID 21913902Carbamic acid, [2-(2-propynyloxy)ethyl]-, 1,1-dimethylethyl ester (9CI)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-hydroxy-ethyl)-carbamic acid tert-butyl ester (1.56 g) in DCM (25 mL) benzyltrimethylammonium chloride (0.18 g) was added. To this solution aqueous 50% NaOH (30 g) and propargyl bromide (1.05 mL of 80% solution in toluene) were added and the mixture was vigorously stirred at room temperature for 3 h. Phases were diluted and separated; the organic phase was washed with water (2×15 mL), dried and evaporated under reduced pressure. The residue was purified by chromatography (silica gel, 0-5% methanol in DCM) to give the title compound as a pale-orange oil (1.53 g); ESMS m/z 222.4 [M+Na]+.

Workup

  1. additionPhases were diluted
  2. customseparated
  3. washthe organic phase was washed with water (2×15 mL)
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography (silica gel, 0-5% methanol in DCM)

Sources & evidence

ORD record
ord-775c027f9fd24ceb8d94c8e949b01ec9
Source dataset
uspto-grants-2010_05
Patent number
US07718621B2

Reaction notes

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