Potassium Carbonate → 1254962-88-3

HRID 1807537Notes

Reaction equation

HRID 1807537 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[C:2]#[C:3][CH2:4]C.C(=O)([O-])[O-].[K+].[K+].[OH:16][N:17]=[C:18](Br)[Br:19]>ClCCl>[CH2:8]([O:7][C:1]([C:2]1[C:18]([Br:19])=[N:17][O:16][C:3]=1[CH3:4])=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 99169Ethyl pent-2-yn-1-oateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromide

Product 1

HCID 666436981254962-88-3Yield 114%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-pentynoate (16.09 mL, 138 mmol) in dichloromethane (80 mL) was added potassium carbonate (20.65 g, 147.9 mmol) and then a solution of hydroxycarbonimidic dibromide (20.0 g, 98.6 mmol) in dichloromethane (100 mL) was added. The reaction mixture was stirred at room temperature over night. The solvent was then removed and purification by filtration (silica, dichloromethane then ethyl acetate) afforded the title compound (26.3 g, 88%) as a light yellow oil. MS: m/e=234.0 [M]+.

Workup

  1. customThe solvent was then removed
  2. custompurification
  3. filtrationby filtration (silica, dichloromethane

Sources & evidence

ORD record
ord-779100dd924a4bdf98d72b49796b577f
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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