Ethyl Bromide → HCID 20872826, compound

HRID 497512Notes

Reaction equation

HRID 497512 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].Br[CH2:20][CH3:21]>CN(C=O)C.CCOC(C)=O>[CH3:16][O:15][C:13](=[O:14])[CH:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:11][CH:10]=1)[CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 120122Methyl 4-butoxyphenylacetate

Product 1

HCID 20872826HCID 20872826, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

(Scheme 2, Compound E) The mixture of methyl 4-butoxyphenylacetate (1.20 g, 5.4 mmol) and NaH (60% in mineral oil, 0.50 g, 12.5 mmol) in DMF (25.0 mL) was stirred at 50° C. for 40 min. Bromoethane (2.0 g, 18.3 mmol) was added and the stirring continued at rt for one hour. The reaction mixture was diluted with EtOAc (300 mL), washed with H2O, and then was dried over Na2SO4. After filtration and concentration in vacuo, the residue was purified by flash chromatography (SiO2: EtOAc/Hexanes). This compound was obtained as a yellow oil (0.85 g, 3.4 mmol, 63% yield). 1H NMR (DMSO-d6) δ 7.16 (d, 2H, J=7.0 Hz), 6.87 (d, 2H, J=8.5 Hz), 3.92 (t, 2H, J=6.5 Hz), 3.55 (s, 3H), 3.45 (t, 1H, J=9.0), 1.93 (m, 1H), 1.63 (m, 2H), 1.42 (m, 2H), 0.97 (t, 3H, J=7.2 Hz), 0.79 (t, 3H, J=4.0 Hz).

Workup

  1. waitthe stirring continued at rt for one hour
  2. washwashed with H2O
  3. dry with materialwas dried over Na2SO4
  4. filtrationAfter filtration and concentration in vacuo
  5. customthe residue was purified by flash chromatography (SiO2: EtOAc/Hexanes)

Sources & evidence

ORD record
ord-20d3ae02a15c4889908fa5163a5c9446
Source dataset
uspto-grants-2005_09
Patent number
US06949574B2

Reaction notes

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