Triethylamine → Ethyl [4-(tetrahydropyran-4-ylsulfanyl)phenyl]acetate

HRID 1350297Notes

Reaction equation

HRID 1350297 reaction equation
CCN(CC)CC.I[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[SH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1>CN(C=O)C>[O:12]1[CH2:13][CH2:14][CH:9]([S:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][CH:21]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27955064-iodotetrahydro-2H-pyranHCID 123300434-Mercapto-phenyl-acetic acid ethyl ester

Product 1

HCID 58860815Ethyl [4-(tetrahydropyran-4-ylsulfanyl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NEt3 (1.3 mL, 9.0 mmol) and 4-iodotetrahydropyran (1.93 g, 9.0 mmol) were added to a stirred solution of ethyl (4-mercaptophenyl)acetate (1.21 g, 6.0 mmol) in anhydrous DMF (10 mL) at 0° C. The mixture was allowed to warm to room temperature over 3d, then the solvents were removed under reduced pressure. The residue was partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (50 mL), the aqueous phase being extracted further with Et2O (45 mL). The combined ethereal extracts were washed with H2O (50 mL), H2O-saturated aqueous Na2CO3 (1:1, 50 mL), and brine (50 mL), before being dried (MgSO4). Filtration, solvent evaporation, and flash chromatography (IH-Et2O, 10:1 to 2:1) afforded the title compound: RF (IH-Et2O, 2:1)=0.31.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was partitioned between Et2O (100 mL) and saturated aqueous NH4Cl (50 mL)
  3. extractionthe aqueous phase being extracted further with Et2O (45 mL)
  4. washThe combined ethereal extracts were washed with H2O (50 mL), H2O-saturated aqueous Na2CO3 (1:1, 50 mL), and brine (50 mL)
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationFiltration, solvent evaporation, and flash chromatography (IH-Et2O, 10:1 to 2:1)

Sources & evidence

ORD record
ord-70786969d76d4fb091f48d4ff19bd46a
Source dataset
uspto-grants-2007_05
Patent number
US07214681B2

Reaction notes

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