Iodoethane → Ethyl 2-(4-(ethylthio)phenyl)acetate

HRID 1777819Notes

Reaction equation

HRID 1777819 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:19][CH3:20].[C:21](OCC)(=O)[CH3:22]>CN(C=O)C.O>[CH2:21]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([S:1][CH2:19][CH3:20])=[CH:7][CH:6]=1)[CH3:22]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 33905114-Mercaptophenylacetic acid

Product 1

HCID 82553740Ethyl 2-(4-(ethylthio)phenyl)acetateYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-mercaptophenyl)acetic acid (32 g, crude, 0.19 mol) in dry DMF (300 mL) was added potassium carbonate (105 g, 0.76 mol) and iodoethane (118 g, 0.76 mol). The reaction mixture was stirred at rt overnight. Ethyl acetate (800 mL) and water (600 mL) were added to the mixture. After partitioning, the aqueous layer was extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine (2×800 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluting with 30:1 petroleum ether:ethyl acetate) to give ethyl2-(4-(ethylthio)phenyl)acetate (15.3 g, 36%) as a yellow oil. LC-MS tR=0.881 min in 5-95AB—1.5 min chromatography (Welch Xtimate C18, 2.1*30 mm, 3 um), MS (ESI) m/z 224.8 [M+H]+. 1H NMR (CDCl3 300 MHz): δ 7.02 (d, J=8.1 Hz, 2H), 6.94 (d, J=8.1 Hz, 2H), 3.89 (q, J=7.2 Hz, 2H), 3.31 (s, 2H), 2.67 (q, J=7.5 Hz, 2H), 1.07-0.97 (m, 6H).

Workup

  1. customAfter partitioning
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×500 mL)
  3. washThe combined organic layers were washed with brine (2×800 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluting with 30:1 petroleum ether:ethyl acetate)

Sources & evidence

ORD record
ord-3a0c2da958134386a62a7e2e0658cb8d
Source dataset
uspto-grants-2016_02
Patent number
US09266886B2

Reaction notes

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