Triethylamine → HCID 59617426, compound

HRID 2276850Notes

Reaction equation

HRID 2276850 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10](OB(O)O)=[CH:9][CH:8]=1)[CH3:2].C(N(CC)CC)C.[C:25]1(=[O:30])[CH2:29][CH2:28][CH:27]=[CH:26]1.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:27]2[CH2:28][CH2:29][C:25](=[O:30])[CH2:26]2)=[CH:9][CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 135882-Cyclopenten-1-oneHCID 516892Sodium BicarbonateHCID 67296509HCID 67296509, compound

Product 1

HCID 59617426HCID 59617426, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Under an argon stream, [4-(3-ethoxy-3-oxopropyl)phenyl]boric acid (2.33 g, 15 mmol) and Rh[(S)-BINAP(nbd)]BF4 (226 mg, 0.25 mmol) was dissolved in a solvent mixture of 1,4-dioxane (30 mL) and water (5 mL), followed by degassing with ultrasonic waves. Then, triethylamine (2.1 mL, 13 mmol) and cyclopentenone (1.1 mL, 13 mmol) were sequentially added, and the mixture was stirred overnight at room temperature. A saturated aqueous sodium bicarbonate solution was added to the reaction solution, and the solvent was distilled off under reduced pressure. The aqueous phase was extracted with ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by column chromatography (ethyl acetate/hexane: 15/85-25/75) to give the title compound (2.76 g, 85%).

Workup

  1. customby degassing with ultrasonic waves
  2. distillationthe solvent was distilled off under reduced pressure
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue obtained
  7. customwas purified by column chromatography (ethyl acetate/hexane: 15/85-25/75)

Sources & evidence

ORD record
ord-58874f87af584f4d8a2d040c3130e58e
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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