Ethyl Acetate → HCID 68800171, compound

HRID 1007910Notes

Reaction equation

HRID 1007910 reaction equation
[F:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][OH:13])=[CH:10][C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].[CH3:20][N:21]([CH2:26][CH2:27][O:28]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:22](=[O:25])[CH2:23]Cl.C(OCC)(=O)C>C(O)(C)(C)C.CN(C)C=O.O>[OH:28][CH2:27][CH2:26][N:21]([CH3:20])[C:22](=[O:25])[CH2:23][O:13][CH2:12][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[S:6][C:2]([F:1])=[CH:3][C:4]=2[CH:10]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 22666547HCID 22666547, compoundHCID 23665647Potassium tert-butoxideHCID 68798711HCID 68798711, compound

Product 1

HCID 68800171HCID 68800171, compoundYield 77.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolvent

Procedure

In a mixture of 4.8 mL of tert-butanol and 1.2 mL of N,N-dimethylformamide is dissolved 0.60 g of 2-(2-fluorobenzo[b]thiophen-5-yl)-1-ethanol, to which are added, at an ice-cooled temperature, 0.45 g of potassium tert-butoxide and 1.81 g of N1-methyl-N1-[2-(trityloxy)ethyl]-2-chloroacetamide. The resulting mixture is stirred at the same temperature as above for 30 minutes and then at ambient temperature for 2 hours. Ethyl acetate and water are added to the reaction mixture, and the organic layer is separated. The solvent is distilled off under reduced pressure. To the residue are added 6 mL of ethanol, 0.6 mL of water and 0.29 g of p-toluenesulfonic acid monohydrate, and the resulting mixture is stirred at ambient temperature overnight. Ethyl acetate and water are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform:methanol=50:1 to 30:1). Thus, 0.74 g of N1-(2-hydroxyethyl)-N1-methyl-2-[2-(2-fluorobenzo[b]-thiophen-5-yl)ethoxy]-acetamide is obtained as an oily product.

Workup

  1. waitat ambient temperature for 2 hours
  2. customthe organic layer is separated
  3. distillationThe solvent is distilled off under reduced pressure
  4. additionTo the residue are added 6 mL of ethanol, 0.6 mL of water and 0.29 g of p-toluenesulfonic acid monohydrate
  5. stirringthe resulting mixture is stirred at ambient temperature overnight
  6. additionEthyl acetate and water are added to the reaction mixture
  7. customthe organic layer is separated
  8. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent is distilled off under reduced pressure
  11. customthe residue is purified by column chromatography (eluent: chloroform:methanol=50:1 to 30:1)

Sources & evidence

ORD record
ord-04164987fe30436ab7b6a2e495ece346
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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