Tetrahydrofuran → HCID 22633969, compound

HRID 2417253Notes

Reaction equation

HRID 2417253 reaction equation
CC(C)([O-:4])C.[K+].[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:8]#[C:9][CH3:10].[CH2:19]1[CH2:23][O:22]C[CH2:20]1>C1COCC1.CN(C=O)C>[CH2:7]([O:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:20][CH2:19][C:23]([OH:22])=[O:4])=[CH:16][CH:17]=1)[C:8]#[C:9][CH3:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 226340454-But-2-ynyloxy-phenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 22633969HCID 22633969, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a 0° C. solution of 1.015 g (8.60 mmol) of potassium t-butoxide suspended in 10 mL of dry THF was added a solution of 1.40 g (8.60 mmol) of 4-but-2-ynyloxy-phenol, dissolved in 30 mL of THF/DMF (5:1). The reaction was stirred at room temperature for 10 minutes and then recooled to 0° C. followed by the addition of 0.66 mL (9.46 mmol) of neat •-propiolactone. The resulting mixture was stirred overnight at room temperature and then concentrated in vacuo. The residue was diluted with ethyl acetate and extracted with saturated sodium bicarbonate solution. The alkaline aqueous extracts were acidified to pH2 with concentrated HCl solution and the precipitated solid was collected by filtration, washed with water and dried in vacuo to provide 0.089 g of the carboxylic acid as a black solid; m.p. 88-92° C. Electrospray Mass Spec: 232.9 (M−H)−

Workup

  1. customTo a 0° C.
  2. customrecooled to 0° C.
  3. stirringThe resulting mixture was stirred overnight at room temperature
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate
  6. extractionextracted with saturated sodium bicarbonate solution
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-bccd6f291a964a8d8c51849f48d32d55
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

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