Hydrochloric Acid → HCID 22644705, compound

HRID 1976381Notes

Reaction equation

HRID 1976381 reaction equation
[CH2:1]([OH:5])[C:2]#[C:3][CH3:4].[H-].[Na+].F[C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]([CH3:26])[CH:19]([CH:23]([CH3:25])[CH3:24])[C:20]([OH:22])=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl>CN(C=O)C.O>[CH2:1]([O:5][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]([CH3:26])[CH:19]([CH:23]([CH3:24])[CH3:25])[C:20]([OH:22])=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]#[C:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 22645018HCID 22645018, compound

Product 1

HCID 22644705HCID 22644705, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3.17 mL (0.042 mol) of 2-butyn-1-ol in 60 ml of DMF at room temperature was added 1.70 g (0.040 mol) 60% sodium hydride. The resulting mixture was stirred for 0.5 h and then a solution of 2.45 g (8.478 mmol) the product of Example 11 dissolved in 20 mL of DMF was added to the reaction. The reaction mixture was then heated to reflux for 24 h, cooled to room temperature and then acidified to pH 2 with 10% HCl solution. After stirring for 1 h the resulting mixture was diluted with water and extracted with ethyl acetate. The combined organics were then dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:2) to provide 1.67 g (58%) of the desired carboxylic acid product as a white solid identical to the product of Example 8.

Workup

  1. additionwas added to the reaction
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux for 24 h
  4. stirringAfter stirring for 1 h the resulting mixture
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organics were then dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:2)

Sources & evidence

ORD record
ord-14a8547664ab4a0d8f01efccc143806b
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

Loading…