Ethyl 3-mercaptopropionate → Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate

HRID 1743658Notes

Reaction equation

HRID 1743658 reaction equation
[H-].[Na+].[SH:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[H][H].[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>CN(C=O)C>[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][S:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 21625Ethyl 3-mercaptopropionateHCID 24758Sodium hydrideHCID 41663BromocresolHCID 178418361HCID 178418361, compound

Product 1

HCID 21964457Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of NaH (60% dispersed in oil, 0.731 g, 21.7 mmol) in dry DMF (15 ml) was added Ethyl 3-mercaptopropionate (2.66 g, 19.8 mmol). When the evolution of hydrogen ceased, 4-Hydroxybenzyl bromide from Step A was added. The reaction mixture was stirred for 16 hours at room temperature, quenched with sat. NH4Cl and concentrated in vacuo. The crude residue was taken in EtOAc and washed 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 (dichloromethane: ethyl acetate, 95:5) to provide the title compound.

Workup

  1. customquenched with sat. NH4Cl
  2. concentrationconcentrated in vacuo
  3. washwashed 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-94acc30ae5c54ffeb65c0801da320dec
Source dataset
uspto-grants-2006_03
Patent number
US07012071B2

Reaction notes

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