Sodium hydride → Ethyl 3-((4-(2-fluorobenzyloxy)phenyl)-methylthio)propionate

HRID 25002

Reaction equation

HRID 25002 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1.[H][H].[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Br>CN(C=O)C>[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][S:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 21964457Ethyl 3-((4-hydroxyphenyl)-methylthio)propionateHCID 178418361HCID 178418361, compound

Product 1

HCID 21964542Ethyl 3-((4-(2-fluorobenzyloxy)phenyl)-methylthio)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (60% dispersed in oil, 0.054 g, 1.3 mmol) in dry DMF (10 ml) was added Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate (Step B, 2.5 g, 1.0 mmol). When the evolution of hydrogen ceased, 2-Fluorobenzyl bromide (0.263 g, 1.3 mmol) was added. The reaction mixture was stirred for 4 hours at room temperature, quenched with sat. NH4Cl, and concentrated in vacuo. The crude residue was taken in EtOAc and washed twice with water and brine. The aqueous layer was washed one more time with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on silica gel column (hex: ethyl acetate, 4:1) to provide the title compound.

Workup

  1. customquenched with sat. NH4Cl
  2. concentrationconcentrated in vacuo
  3. washwashed twice with water and brine
  4. washThe aqueous layer was washed one more time with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe purification

Sources & evidence

ORD record
ord-bef4aa0a002b41ddad0dd66ab634e9b6
Source dataset
uspto-grants-2005_02
Patent number
US06858602B2

Linked notes

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