Propargyl bromide → HCID 178458211, compound

HRID 2121909Notes

Reaction equation

HRID 2121909 reaction equation
[OH:1][C@H:2]([CH3:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[NH:6][N:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]#[CH:23]>C(O)C.O>[CH2:23]([O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][N:5]=[C:4]2[CH2:3][C@H:2]([OH:1])[CH3:14])[C:22]#[CH:21]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 178462268HCID 178462268, compound

Product 1

HCID 178458211HCID 178458211, compoundYield 69.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred mixture of the product from Step A (1.50 g, 7.81 mmol) in a mixture of ethanol in water (50 mL/10 mL) was added potassium carbonate (1.62 g, 11.7 mmol) and propargyl bromide (80% in toluene, 1.74 g, 1.30 mL, 11.7 mmol). The mixture was heated at 75° C. for 2 hours under nitrogen, evaporated to dryness, mixed with a saturated aqueous solution of sodium bicarbonate (50 mL) and extracted with ethyl acetate. Chromatography on silica (gradient, 25% to 95% ethyl acetate in hexane) gave an oil (1.25 g, 69%): LC/MS (+APCI) m/z 231 (M+H).

Workup

  1. customevaporated to dryness
  2. additionmixed with a saturated aqueous solution of sodium bicarbonate (50 mL)
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-20069fe05ea0487a9ab5fc5e071a5365
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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