3-Butyn-1-OL → HCID 59557720, compound

HRID 1175329Notes

Reaction equation

HRID 1175329 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18]Br.[OH-].[Na+].[CH2:22]([OH:26])[CH2:23][C:24]#[CH:25]>C1(C)C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[I-].O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][O:26][CH2:22][CH2:23][C:24]#[CH:25]

Participants

7

Reactant 3

HCID 135663-Butyn-1-OLHCID 14798Sodium HydroxideHCID 68740201HCID 68740201, compound

Product 1

HCID 59557720HCID 59557720, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-bromo-2-(bromomethyl)-4-chloro-5-(4-ethylbenzyl)benzene (200 mg, 0.497 mmol) in toluene (2 mL) was added NaOH (60 mg, 1.5 mmol), but-3-yn-1-ol (53 mg, 1.17 mmol) and TBAI (8.5 mg, 0.023 mmol) successively. After stirring overnight at 70° C., the solution was diluted with water. The solution was extracted with ethyl acetate and the extracts were washed with a saturated solution of NH4Cl, followed by drying over Na2SO4. The solution was concentrated and the resulting residue was purified by preparative TLC to afford 96 mg of title product.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe extracts were washed with a saturated solution of NH4Cl
  3. dry with materialby drying over Na2SO4
  4. concentrationThe solution was concentrated
  5. customthe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-ed37bd40fd3244a3bec8378247ffc831
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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