Sodium Hydroxide → HCID 69736878, compound

HRID 2086184Notes

Reaction equation

HRID 2086184 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]#[CH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[B]1OC2C(=CC=CC=2)O1.Br[C:22]1[S:26][C:25]([CH2:27][CH2:28][C:29]2([CH3:35])[CH2:33][O:32][C:31](=[O:34])[NH:30]2)=[CH:24][CH:23]=1.[O-]CC.[Na+].[OH-].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:35][C:29]1([CH2:28][CH2:27][C:25]2[S:26][C:22]([CH:11]=[CH:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:23][CH:24]=2)[CH2:33][O:32][C:31](=[O:34])[NH:30]1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 745735-Phenyl-1-pentyneHCID 2723922Sodium ethoxideHCID 6327445BenzcatechinboraneHCID 22279728HCID 22279728, compound

Product 1

HCID 69736878HCID 69736878, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To 5-phenylpent-1-yne (0.38 ml, 2.58 mmol) was added catecholborane (500 mg, 1.72 mmol) at room temperature, and the mixture was stirred at 60° C. for 3 hours. After the reaction solution was cooled down to room temperature, toluene (5.0 ml), 4-[2-(5-bromothiophen-2-yl)]ethyl-4-methyloxazolidin-2-one (500 mg, 1.72 mmol) obtained in Example 1(f), bis(triphenylphosphine)palladium chloride (119 mg, 0.17 mmol), and sodium ethoxide (0.83 ml, 20% ethanol solution) were added thereto at room temperature. The reaction mixture was stirred for 2 hours at 60° C., cooled down to room temperature, and then 1N sodium hydroxide was added thereto. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with water and then with a saturated aqueous sodium chloride solution. After the ethyl acetate layer was dried over anhydrous sodium sulfate, the solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (378 mg, 68% yield).

Workup

  1. temperatureAfter the reaction solution was cooled down to room temperature
  2. customat room temperature
  3. stirringThe reaction mixture was stirred for 2 hours at 60° C.
  4. temperaturecooled down to room temperature
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with water
  7. dry with materialAfter the ethyl acetate layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated in vacuo
  9. customThe residue was purified by preparative thin-layer chromatography (elution solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-98b8e1343e2247028c31b4d3bf56e5eb
Source dataset
uspto-grants-2004_04
Patent number
US06723745B2

Reaction notes

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